| Team | Opponent | Date | Time | Location | Result | Advantage | Status |
|---|---|---|---|---|---|---|---|
| Girl's Varsity Soccer | @ Middle School Soccer Jamboree | Sep 10 | 3:30 PM | Ethel Walker School | - | Away | |
| Girl's Varsity Soccer | @ Renbrook School | Sep 16 | 4:00 PM | Renbrook School | - | Away | |
| Boy's Varsity Soccer | @ Trinity Pawling School | Sep 16 | 4:15 PM | Trinity Pawling School | - | Away | |
| Varsity Volleyball | @ Miss Porter's School | Sep 17 | 3:15 PM | Miss Porter's School | - | Away | |
| Varsity Field Hockey | vs. Westminster School | Sep 17 | 3:15 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Sep 17 | 3:30 PM | Kent School | - | Away | |
| Varsity Cross Country | @ Rhino Run - Taft School Invitational | Sep 17 | 4:00 PM | Taft School | - | Away | |
| Varsity Football | @ Brunswick School | Sep 18 | 3:30 PM | Brunswick School | - | Away | |
| Varsity B Field Hockey | vs. Renbrook School | Sep 18 | 3:45 PM | Home | - | Home | |
| Junior Blue Soccer | @ Washington Montessori School (WMS) | Sep 18 | 3:45 PM | Washington Montessori School (WMS) | - | Away | |
| Varsity B Soccer | @ Masters School (CT) | Sep 18 | 4:00 PM | The Masters School (CT) | - | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Sep 19 | 3:15 PM | Indian Mountain School | - | Away | |
| Varsity Field Hockey | @ Ethel Walker School | Sep 19 | 3:30 PM | Ethel Walker School | - | Away | |
| Varsity B Soccer | @ Mizzentop | Sep 19 | 3:30 PM | Mizzentop | - | Away | |
| Junior Blue Soccer | vs. Indian Mountain School | Sep 19 | 3:30 PM | Home | - | Home | |
| Boy's Varsity Soccer | vs. Taft School | Sep 19 | 4:00 PM | Home | - | Home | |
| Girl's Varsity Soccer | vs. Millbrook School | Sep 19 | 4:15 PM | Home | - | Home | |
| Varsity Volleyball | vs. Berkshire School | Sep 19 | 4:30 PM | Home | - | Home | |
| Girl's Varsity Soccer | vs. Canterbury School | Sep 20 | 1:00 PM | Home | - | Home | |
| Boy's Varsity Soccer | @ Choate Rosemary Hall | Sep 20 | 2:30 PM | Choate Rosemary Hall | - | Away | |
| Boy's Varsity Soccer | vs. Avon Old Farms School | Sep 24 | 3:15 PM | Home | - | Home | |
| Girl's Varsity Soccer | vs. Berkshire School | Sep 24 | 3:15 PM | Home | - | Home | |
| Varsity Volleyball | @ Cheshire Academy | Sep 24 | 3:15 PM | Cheshire Academy | - | Away | |
| Varsity Field Hockey | vs. Berkshire School | Sep 24 | 3:15 PM | Home | - | Home | |
| Varsity B Volleyball | vs. Miss Porter's School | Sep 24 | 3:15 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | vs. HMBL Race | Sep 24 | 3:30 PM | Home | - | Home | |
| Varsity B Soccer | @ Renbrook School | Sep 24 | 3:30 PM | Renbrook School | - | Away | |
| Junior Blue Soccer | @ Mizzentop | Sep 25 | 4:00 PM | Mizzentop | - | Away | |
| Varsity B Field Hockey | vs. Upland Country Day School | Sep 26 | 1:45 PM | Home | - | Home | |
| Varsity Volleyball | @ Ethel Walker School | Sep 26 | 3:00 PM | Ethel Walker School | - | Away | |
| Varsity Cross Country | vs. Dutchess Day School | Sep 26 | 3:15 PM | Home | - | Home | |
| Varsity B Soccer | vs. Sherman Middle School | Sep 26 | 3:45 PM | Home | - | Home | |
| Boy's Varsity Soccer | @ Frederick Gunn School | Sep 26 | 4:00 PM | Frederick Gunn School | - | Away | |
| Varsity Field Hockey | vs. Miss Porter's School | Sep 27 | 11:00 AM | Home | - | Home | |
| Varsity Football | vs. Avon Old Farms School | Sep 27 | 2:30 PM | Home | - | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Sep 30 | 3:45 PM | Home | - | Home | |
| Varsity B Soccer | vs. Dutchess Day School | Sep 30 | 3:45 PM | Home | - | Home | |
| Junior Blue Soccer | @ Dutchess Day School | Sep 30 | 4:00 PM | Dutchess Day School | - | Away | |
| Varsity B Volleyball | @ Oakwood Friends School | Sep 30 | 4:00 PM | Oakwood Friends School | - | Away | |
| Varsity Field Hockey | vs. Canterbury School | Oct 1 | 3:15 PM | Home | - | Home | |
| Varsity Volleyball | vs. Kent School | Oct 1 | 3:15 PM | Home | - | Home | |
| Girl's Varsity Soccer | @ Canterbury School | Oct 1 | 3:15 PM | Canterbury School | - | Away | |
| Varsity Football | vs. Brunswick School | Oct 1 | 3:30 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 1 | 3:30 PM | Indian Mountain School | - | Away | |
| Varsity B Soccer | vs. Upland Country Day School | Oct 2 | 4:00 PM | Home | - | Home | |
| Varsity B Soccer | @ Dutchess Day Soccer Tournament 7 v.7 | Oct 3 | 3:00 PM | Dutchess Day School | - | Away | |
| Junior Blue Soccer | @ Dutchess Day Soccer Tournament 7 v.7 | Oct 3 | 3:00 PM | Dutchess Day School | - | Away | |
| Girl's Varsity Soccer | vs. Indian Mountain School | Oct 3 | 3:15 PM | Home | - | Home | |
| Varsity B Volleyball | vs. Indian Mountain School | Oct 3 | 3:15 PM | Home | - | Home | |
| Varsity Volleyball | @ Hopkins School | Oct 3 | 4:00 PM | Hopkins School | - | Away | |
| Boy's Varsity Soccer | @ Millbrook School | Oct 3 | 4:00 PM | Millbrook School | - | Away | |
| Varsity Field Hockey | vs. Frederick Gunn School | Oct 3 | 4:15 PM | Home | - | Home | |
| Girl's Varsity Soccer | @ Miss Porter's School | Oct 4 | 12:00 PM | Miss Porter's School | - | Away | |
| Varsity B Soccer | vs. Mizzentop | Oct 6 | 3:45 PM | Home | - | Home | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 7 | 4:00 PM | Dutchess Day School | - | Away | |
| Varsity Volleyball | @ Hotchkiss School | Oct 8 | 3:15 PM | Hotchkiss School | - | Away | |
| Girl's Varsity Soccer | vs. Miss Porter's School | Oct 8 | 3:15 PM | Home | - | Home | |
| Boy's Varsity Soccer | vs. Kent School | Oct 8 | 3:15 PM | Home | - | Home | |
| Junior Blue Soccer | @ Indian Mountain School | Oct 8 | 3:30 PM | Indian Mountain School | - | Away | |
| Varsity Cross Country | @ Millbrook School | Oct 8 | 3:30 PM | Millbrook School | - | Away | |
| Varsity Field Hockey | @ Suffield Academy | Oct 8 | 3:30 PM | Suffield Academy | - | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 8 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity B Volleyball | vs. Oakwood Friends School | Oct 8 | 4:00 PM | Home | - | Home | |
| Boy's Varsity Soccer | @ Indian Mountain School | Oct 10 | 3:15 PM | Indian Mountain School | - | Away | |
| Varsity Cross Country | vs. Indian Mountain School | Oct 10 | 3:30 PM | Home | - | Home | |
| Varsity Volleyball | @ Taft School | Oct 10 | 4:00 PM | Taft School | - | Away | |
| Varsity Football | @ Avon Old Farms School | Oct 10 | 4:00 PM | Avon Old Farms School | - | Away | |
| Varsity B Volleyball | @ Hopkins School | Oct 10 | 4:00 PM | Hopkins School | - | Away | |
| Varsity Field Hockey | @ Canterbury School | Oct 11 | 2:30 PM | Canterbury School | - | Away | |
| Varsity B Soccer | vs. Trinity Pawling School | Oct 14 | 4:00 PM | Home | - | Home | |
| Girl's Varsity Soccer | @ Ethel Walker School | Oct 14 | 4:30 PM | Ethel Walker School | - | Away | |
| Girl's Varsity Soccer | @ Kingswood-Oxford School | Oct 15 | 3:15 PM | Kingswood-Oxford School | - | Away | |
| Boy's Varsity Soccer | @ Avon Old Farms School | Oct 15 | 3:15 PM | Avon Old Farms School | - | Away | |
| Varsity B Soccer | @ Indian Mountain School | Oct 15 | 3:15 PM | Indian Mountain School | - | Away | |
| Varsity Volleyball | vs. Indian Mountain School | Oct 15 | 3:15 PM | Home | - | Home | |
| Varsity Field Hockey | vs. Choate Rosemary Hall | Oct 15 | 3:15 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 15 | 3:30 PM | South Kent School | - | Away | |
| Varsity B Volleyball | vs. Hopkins School | Oct 15 | 3:45 PM | Home | - | Home | |
| Junior Blue Soccer | vs. Mizzentop | Oct 15 | 3:45 PM | Home | - | Home | |
| Junior Blue Soccer | vs. Renbrook School | Oct 16 | 3:45 PM | Home | - | Home | |
| Varsity Cross Country | vs. Washington Montessori School (WMS) | Oct 16 | 3:45 PM | Home | - | Home | |
| Varsity Volleyball | vs. Taft School | Oct 18 | 2:30 PM | Home | - | Home | |
| Varsity Football | vs. Buckley School | Oct 18 | 2:30 PM | Home | - | Home | |
| Boy's Varsity Soccer | vs. Wooster School | Oct 18 | 2:30 PM | Home | - | Home | |
| Girl's Varsity Soccer | vs. Frederick Gunn School | Oct 18 | 2:30 PM | Home | - | Home | |
| Varsity Field Hockey | vs. Frederick Gunn School | Oct 18 | 2:30 PM | Home | - | Home | |
| Varsity B Volleyball | vs. Masters School (CT) | Oct 21 | 3:45 PM | Home | - | Home | |
| Varsity Field Hockey | @ Renbrook School | Oct 21 | 4:00 PM | Renbrook School | - | Away | |
| Varsity B Soccer | @ Trinity Pawling School | Oct 21 | 4:00 PM | Trinity Pawling School | - | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 21 | 4:00 PM | Dutchess Day School | - | Away | |
| Varsity Cross Country | @ Indian Mountain School | Oct 22 | 3:15 PM | Indian Mountain School | - | Away | |
| Junior Blue Soccer | vs. Indian Mountain School | Oct 22 | 3:30 PM | Home | - | Home | |
| Varsity Football | @ Hopkins School | Oct 22 | 3:30 PM | Hopkins School | - | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 22 | 3:30 PM | Trinity Pawling School | - | Away | |
| Junior Blue Soccer | vs. Washington Montessori School (WMS) | Oct 23 | 3:45 PM | Home | - | Home | |
| Varsity B Soccer | vs. Masters School (CT) | Oct 23 | 3:45 PM | Home | - | Home | |
| Girl's Varsity Soccer | @ Washington Montessori School (WMS) | Oct 23 | 3:45 PM | Washington Montessori School (WMS) | - | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 24 | 3:15 PM | Indian Mountain School | - | Away | |
| Varsity Cross Country | @ Dutchess Day School | Oct 24 | 3:30 PM | Dutchess Day School | - | Away | |
| Junior Blue Soccer | vs. Dutchess Day School | Oct 28 | 3:45 PM | Home | - | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 28 | 3:45 PM | Home | - | Home | |
| Varsity B Soccer | @ Dutchess Day School | Oct 28 | 4:00 PM | Dutchess Day School | - | Away | |
| Varsity B Volleyball | @ Masters School (CT) | Oct 28 | 4:00 PM | The Masters School (CT) | - | Away | |
| Varsity Field Hockey | @ Westminster School | Oct 29 | 3:15 PM | Westminster School | - | Away | |
| Boy's Varsity Soccer | vs. Westminster School | Oct 29 | 3:15 PM | Home | - | Home | |
| Girl's Varsity Soccer | @ Berkshire School | Oct 29 | 3:15 PM | Berkshire School | - | Away | |
| Varsity Volleyball | vs. Choate Rosemary Hall | Oct 29 | 3:15 PM | Home | - | Home | |
| Varsity Cross Country | vs. Kingswood-Oxford School | Oct 29 | 3:30 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 29 | 3:30 PM | Berkshire School | - | Away | |
| Varsity B Soccer | @ Sherman Middle School | Oct 30 | 3:45 PM | Sherman Middle School | - | Away | |
| Boy's Varsity Soccer | @ Eaglebrook Boys Soccer Tournament | Nov 1 | 10:00 AM | Eaglebrook School | - | Away | |
| Girl's Varsity Soccer | @ IMS Girls Soccer Tournament | Nov 1 | 10:00 AM | Indian Mountain School | - | Away | |
| Varsity Volleyball | vs. Rick Spooner Volleyball Classic | Nov 1 | 2:00 PM | Home | - | Home | |
| Varsity B Soccer | vs. Washington Montessori School (WMS) | Nov 3 | 3:30 PM | Home | - | Home | |
| Girl's Varsity Soccer | vs. Westminster School | Nov 5 | 3:00 PM | Home | - | Home | |
| Varsity Football | vs. Berkshire School | Nov 5 | 3:00 PM | Home | - | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Championships | Nov 5 | 3:00 PM | Norbrook Farm | - | Away | |
| Varsity B Volleyball | vs. Forman School | Nov 5 | 3:15 PM | Home | - | Home | |
| Varsity Volleyball | vs. Kingswood-Oxford School | Nov 5 | 3:15 PM | Home | - | Home | |
| Boy's Varsity Soccer | @ Salisbury School | Nov 5 | 3:15 PM | Salisbury School | - | Away | |
| Varsity Cross Country | @ Washington Montessori School (WMS) | Nov 5 | 3:30 PM | Washington Montessori School (WMS) | - | Away | |
| Girl's Varsity Soccer | @ Indian Mountain School | Nov 6 | 6:30 PM | Hotchkiss School | - | Away | |
| Boy's Varsity Soccer | vs. Indian Mountain School | Nov 7 | 2:45 PM | Home | - | Home | |
| Varsity B Soccer | vs. Indian Mountain School | Nov 7 | 2:45 PM | Home | - | Home | |
| Varsity Cross Country | @ Indian Mountain School | Nov 7 | 2:45 PM | Indian Mountain School | - | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Nov 7 | 2:45 PM | Indian Mountain School | - | Away | |
| Varsity Volleyball | @ Indian Mountain School | Nov 7 | 3:15 PM | Indian Mountain School | - | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Nov 7 | 3:15 PM | Home | - | Home | |
| No events found. | |||||||
| Team | Opponent | Date | Time | Location | Result | Advantage | Status |
|---|---|---|---|---|---|---|---|
| Boy's Varsity Soccer | vs. Trinity Pawling School | Sep 17 | 4:30 PM | Home | 10 - 0 | Home | |
| Varsity Volleyball | vs. Miss Porter's School | Sep 18 | 3:00 PM | Home | 3 - 0 | Home | |
| Varsity Field Hockey | @ Westminster School | Sep 18 | 3:15 PM | Westminster School | 1 - 0 | Away | |
| Girl's Varsity Soccer | vs. Renbrook School | Sep 18 | 3:45 PM | Home | 4 - 2 | Home | |
| Varsity Cross Country | @ Taft School | Sep 18 | 4:00 PM | Taft School | - | Away | |
| Junior Blue Soccer | vs. Washington Montessori School (WMS) | Sep 19 | 3:45 PM | Home | 8 - 2 | Home | |
| Varsity B Field Hockey | @ Renbrook School | Sep 19 | 4:00 PM | Renbrook School | 1 - 6 | Away | |
| Varsity Football | @ Taft School | Sep 20 | 3:00 PM | Home | - | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Sep 20 | 3:15 PM | Home | 1 - 2 | Home | |
| Varsity Volleyball | @ Berkshire School | Sep 20 | 3:30 PM | Berkshire School | 3 - 0 | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Sep 20 | 3:30 PM | Indian Mountain School | 6 - 0 | Away | |
| Varsity B Soccer | vs. Mizzentop | Sep 20 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity Soccer | @ Millbrook School | Sep 20 | 4:15 PM | Millbrook School | 7 - 1 | Away | |
| Boy's Varsity Soccer | @ Taft School | Sep 20 | 4:15 PM | Taft School | 3 - 2 | Away | |
| Varsity Field Hockey | vs. Ethel Walker School | Sep 20 | 4:45 PM | Home | 4 - 0 | Home | |
| Boy's Varsity Soccer | vs. Choate Rosemary Hall | Sep 21 | 2:30 PM | Home | 2 - 2 | Home | |
| Girl's Varsity Soccer | vs. Canterbury School | Sep 21 | 2:30 PM | Home | 6 - 4 | Home | |
| Varsity B Soccer | vs. Renbrook School | Sep 24 | 3:45 PM | Home | 0 - 6 | Home | |
| Varsity B Volleyball | @ Miss Porter's School | Sep 25 | 3:00 PM | Miss Porter's School | 0 - 3 | Away | |
| Boy's Varsity Soccer | @ Avon Old Farms School | Sep 25 | 3:15 PM | Avon Old Farms School | 10 - 0 | Away | |
| Varsity Field Hockey | @ Berkshire School | Sep 25 | 3:15 PM | Berkshire School | 1 - 0 | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Sep 25 | 3:30 PM | Kent School | - | Away | |
| Girl's Varsity Soccer | @ Berkshire School | Sep 25 | 3:30 PM | Berkshire School | 5 - 2 | Away | |
| Varsity B Field Hockey | vs. Mizzentop | Sep 25 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity B Soccer | vs. Upland Country Day School | Sep 26 | 3:45 PM | Home | 2 - 3 | Home | |
| Junior Blue Soccer | vs. Mizzentop | Sep 26 | 3:45 PM | Home | 8 - 0 | Home | |
| Varsity B Soccer | vs. Upland Country Day School | Sep 27 | 2:45 PM | Home | 1 - 1 | Home | |
| Varsity B Field Hockey | vs. Upland Country Day School | Sep 27 | 2:45 PM | Home | 1 - 0 | Home | |
| Varsity Volleyball | @ Rectory School | Sep 27 | 3:00 PM | Ethel Walker School | 1 - 2 | Away | |
| Varsity Cross Country | vs. Indian Mountain School | Sep 27 | 3:15 PM | Home | 61 - 46 | Home | |
| Boy's Varsity Soccer | vs. Frederick Gunn School | Sep 27 | 4:00 PM | Home | 2 - 5 | Home | |
| Varsity Field Hockey | @ Miss Porter's School | Sep 28 | 10:00 AM | Miss Porter's School | 7 - 1 | Away | |
| Varsity Football | @ Avon Old Farms School | Sep 28 | 2:30 PM | Avon Old Farms School | 14 - 28 | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 1 | 3:45 PM | Dutchess Day School | 0 - 0 | Away | |
| Junior Blue Soccer | vs. Dutchess Day School | Oct 1 | 3:45 PM | Home | 5 - 1 | Home | |
| Varsity B Soccer | @ Dutchess Day School | Oct 1 | 3:45 PM | Home | 2 - 5 | Away | |
| Varsity B Volleyball | vs. Oakwood Friends School | Oct 1 | 4:00 PM | Home | 3 - 0 | Home | |
| Girl's Varsity Soccer | @ Canterbury School | Oct 2 | 3:00 PM | Canterbury School | 2 - 0 | Away | |
| Varsity Field Hockey | @ Canterbury School | Oct 2 | 3:00 PM | Canterbury School | 4 - 0 | Away | |
| Boy's Varsity Soccer | vs. Hotchkiss School | Oct 2 | 3:15 PM | Home | 4 - 3 | Home | |
| Varsity Volleyball | vs. Kent School | Oct 2 | 3:15 PM | Home | 2 - 3 | Home | |
| Varsity Football | @ Berkshire School | Oct 2 | 3:15 PM | Berkshire School | 0 - 21 | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 2 | 3:30 PM | Indian Mountain School | - | Away | |
| Junior Blue Soccer | @ Washington Montessori School (WMS) | Oct 2 | 3:45 PM | Washington Montessori School (WMS) | 4 - 1 | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 4 | 3:00 PM | Indian Mountain School | 1 - 3 | Away | |
| Junior Blue Soccer | @ Dutchess Day Soccer Tournament 7 v.7 | Oct 4 | 3:15 PM | Dutchess Day School | - | Away | |
| Varsity B Soccer | @ Dutchess Day Soccer Tournament 7 v.7 | Oct 4 | 3:15 PM | Dutchess Day School | - | Away | |
| Girl's Varsity Soccer | @ Indian Mountain School | Oct 4 | 3:15 PM | Indian Mountain School | 2 - 6 | Away | |
| Varsity Field Hockey | vs. Frederick Gunn School | Oct 4 | 4:15 PM | Home | 4 - 0 | Home | |
| Boy's Varsity Soccer | vs. Millbrook School | Oct 4 | 4:30 PM | Home | 7 - 2 | Home | |
| Varsity Volleyball | vs. Hopkins School | Oct 4 | 4:30 PM | Home | 3 - 1 | Home | |
| Girl's Varsity Soccer | vs. Miss Porter's School | Oct 5 | 1:00 PM | Home | 6 - 0 | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 8 | 3:45 PM | Home | 0 - 0 | Home | |
| Varsity B Soccer | @ Mizzentop | Oct 8 | 4:00 PM | Mizzentop | - | Away | Cancelled |
| Varsity Volleyball | @ Kent School | Oct 8 | 4:15 PM | Kent School | - | Away | Cancelled |
| Girl's Varsity Soccer | @ Miss Porter's School | Oct 9 | 3:00 PM | Miss Porter's School | 2 - 0 | Away | |
| Boy's Varsity Soccer | @ Kent School | Oct 9 | 3:15 PM | Kent School | 7 - 0 | Away | |
| Varsity Volleyball | vs. Hotchkiss School | Oct 9 | 3:15 PM | Home | 0 - 3 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Oct 9 | 3:15 PM | Home | 8 - 0 | Home | |
| Varsity Field Hockey | vs. Hotchkiss School | Oct 9 | 3:15 PM | Home | 1 - 0 | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 9 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity Cross Country | @ Millbrook School | Oct 9 | 3:30 PM | Millbrook School | - | Away | |
| Varsity B Soccer | vs. Washington Montessori School (WMS) | Oct 10 | 3:45 PM | Home | 6 - 1 | Home | |
| Varsity Cross Country | @ Indian Mountain School | Oct 11 | 3:15 PM | Indian Mountain School | - | Away | |
| Boy's Varsity Soccer | vs. Indian Mountain School | Oct 11 | 3:15 PM | Home | 1 - 3 | Home | |
| Girl's Varsity Soccer | @ Choate Rosemary Hall | Oct 11 | 4:00 PM | Choate Rosemary Hall | - | Away | Cancelled |
| Varsity Volleyball | @ Taft School | Oct 11 | 4:00 PM | Taft School | 3 - 1 | Away | |
| Varsity B Volleyball | @ Hopkins School | Oct 11 | 4:00 PM | Hopkins School | 1 - 2 | Away | |
| Varsity Football | vs. Avon Old Farms School | Oct 11 | 4:00 PM | Home | 8 - 14 | Home | |
| Varsity Field Hockey | vs. Canterbury School | Oct 12 | 2:30 PM | Home | - | Home | Cancelled |
| Varsity B Soccer | @ Trinity Pawling School | Oct 15 | 4:00 PM | Trinity Pawling School | 2 - 3 | Away | |
| Girl's Varsity Soccer | vs. Ethel Walker School | Oct 15 | 5:00 PM | Home | 4 - 0 | Home | |
| Girl's Varsity Soccer | vs. Kingswood-Oxford School | Oct 16 | 3:15 PM | Home | 5 - 10 | Home | |
| Boy's Varsity Soccer | vs. Avon Old Farms School | Oct 16 | 3:15 PM | Home | 5 - 2 | Home | |
| Varsity B Soccer | vs. Indian Mountain School | Oct 16 | 3:15 PM | Home | 1 - 2 | Home | |
| Varsity Football | vs. Kingswood-Oxford School | Oct 16 | 3:15 PM | Home | 35 - 10 | Home | |
| Varsity B Volleyball | vs. Hopkins School | Oct 16 | 3:15 PM | Home | 1 - 3 | Home | |
| Varsity Volleyball | @ Indian Mountain School | Oct 16 | 3:15 PM | Indian Mountain School | 3 - 1 | Away | |
| Varsity Field Hockey | @ Choate Rosemary Hall | Oct 16 | 3:30 PM | Choate Rosemary Hall | 0 - 2 | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 16 | 3:30 PM | South Kent School | - | Away | |
| Varsity B Field Hockey | @ Mizzentop | Oct 16 | 3:45 PM | Mizzentop | - | Away | Cancelled |
| Junior Blue Soccer | @ Mizzentop | Oct 16 | 3:45 PM | Mizzentop | 4 - 1 | Away | |
| Varsity Cross Country | vs. Washington Montessori School (WMS) | Oct 17 | 3:45 PM | Home | 33 - 117 | Home | |
| Junior Blue Soccer | @ Renbrook School | Oct 17 | 4:00 PM | Renbrook School | 0 - 2 | Away | |
| Varsity B Volleyball | @ Oakwood Friends School | Oct 17 | 4:00 PM | Oakwood Friends School | 2 - 1 | Away | |
| Varsity Volleyball | vs. Taft School | Oct 19 | 2:30 PM | Home | 3 - 0 | Home | |
| Boy's Varsity Soccer | vs. Wooster School | Oct 19 | 2:30 PM | Home | 7 - 0 | Home | |
| Girl's Varsity Soccer | vs. Frederick Gunn School | Oct 19 | 2:30 PM | Home | 5 - 2 | Home | |
| Varsity Field Hockey | vs. Frederick Gunn School | Oct 19 | 2:30 PM | Home | 5 - 0 | Home | |
| Varsity Field Hockey | vs. Renbrook School | Oct 22 | 3:45 PM | Home | 6 - 0 | Home | |
| Varsity B Soccer | vs. Trinity Pawling School | Oct 22 | 3:45 PM | Home | 0 - 3 | Home | |
| Junior Blue Soccer | @ Indian Mountain School | Oct 23 | 3:15 PM | Indian Mountain School | 4 - 0 | Away | |
| Varsity Football | vs. Hopkins School | Oct 23 | 3:30 PM | Home | 36 - 34 | Home | |
| Varsity B Volleyball | @ Hotchkiss School | Oct 23 | 3:30 PM | Hotchkiss School | 0 - 3 | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 23 | 3:30 PM | Trinity Pawling School | - | Away | |
| Girl's Varsity Soccer | @ Washington Montessori School (WMS) | Oct 23 | 3:45 PM | Washington Montessori School (WMS) | 3 - 1 | Away | |
| Varsity Cross Country | @ Indian Mountain School | Oct 23 | 4:00 PM | Indian Mountain School | 40 - 44 | Away | |
| Junior Blue Soccer | @ Washington Montessori School (WMS) | Oct 24 | 3:45 PM | Washington Montessori School (WMS) | 3 - 1 | Away | |
| Varsity B Soccer | @ Mizzentop | Oct 24 | 3:45 PM | Home | 0 - 4 | Away | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 24 | 4:00 PM | Home | 1 - 2 | Home | |
| Varsity B Field Hockey | @ Mizzentop | Oct 24 | 4:00 PM | Mizzentop | - | Away | Cancelled |
| Varsity B Volleyball | vs. Indian Mountain School | Oct 25 | 3:15 PM | Home | 1 - 3 | Home | |
| Varsity B Soccer | vs. Dutchess Day School | Oct 29 | 3:45 PM | Home | 1 - 0 | Home | |
| Junior Blue Soccer | @ Dutchess Day School | Oct 29 | 3:45 PM | Dutchess Day School | 3 - 1 | Away | |
| Girl's Varsity Soccer | vs. Berkshire School | Oct 30 | 3:00 PM | Home | 6 - 1 | Home | |
| Boy's Varsity Soccer | @ Westminster School | Oct 30 | 3:15 PM | Westminster School | 5 - 1 | Away | |
| Varsity Cross Country | vs. Kingswood-Oxford School | Oct 30 | 3:15 PM | Kingswood-Oxford School | - | Home | Cancelled |
| Varsity Field Hockey | vs. Westminster School | Oct 30 | 3:15 PM | Home | 5 - 0 | Home | |
| Blue Dog Bikes - Racing Team | @ HMBL Race | Oct 30 | 3:30 PM | Berkshire School | - | Away | |
| Varsity Volleyball | @ Choate Rosemary Hall | Oct 30 | 3:30 PM | Choate Rosemary Hall | 0 - 3 | Away | |
| Varsity Football | @ Brunswick School | Oct 30 | 3:30 PM | Brunswick School | 27 - 21 | Away | |
| Varsity B Field Hockey | vs. Mizzentop | Oct 31 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity B Field Hockey | @ Dutchess Day School | Nov 1 | 3:30 PM | Dutchess Day School | 0 - 3 | Away | |
| Varsity B Soccer | vs. Sherman Middle School | Nov 1 | 3:30 PM | Home | 5 - 1 | Home | |
| Varsity B Volleyball | vs. Indian Mountain School | Nov 1 | 3:30 PM | Home | 3 - 1 | Home | |
| Varsity Field Hockey | @ Frederick Gunn School | Nov 1 | 4:00 PM | Frederick Gunn School | - | Away | Cancelled |
| Boy's Varsity Soccer | @ Eaglebrook Boys Soccer Tournament | Nov 2 | 8:00 AM | Eaglebrook School | - | Away | |
| Girl's Varsity Soccer | @ IMS Girls Soccer Tournament | Nov 2 | 8:00 AM | Indian Mountain School | - | Away | |
| Varsity Volleyball | vs. Rick Spooner Volleyball Classic | Nov 2 | 2:00 PM | Home | - | Home | |
| Varsity Football | @ Kingswood-Oxford School | Nov 6 | 3:00 PM | Home | 21 - 0 | Away | |
| Varsity Field Hockey | @ Hotchkiss School | Nov 6 | 3:00 PM | Hotchkiss School | 5 - 0 | Away | |
| Blue Dog Bikes - Racing Team | @ HMBL Championships | Nov 6 | 3:00 PM | Norbrook Farm | - | Away | |
| Varsity Volleyball | @ Kingswood-Oxford School | Nov 6 | 3:15 PM | Kingswood-Oxford School | 3 - 0 | Away | |
| Varsity B Volleyball | vs. Forman School | Nov 6 | 3:15 PM | Home | 3 - 1 | Home | |
| Boy's Varsity Soccer | vs. Salisbury School | Nov 6 | 3:15 PM | Home | 2 - 1 | Home | |
| Girl's Varsity Soccer | vs. Washington Montessori School (WMS) | Nov 6 | 3:30 PM | Home | 9 - 2 | Home | |
| Varsity Cross Country | @ Washington Montessori School (WMS) | Nov 6 | 3:30 PM | Washington Montessori School (WMS) | - | Away | |
| Boy's Varsity Soccer | @ Indian Mountain School | Nov 7 | 6:30 PM | Hotchkiss School | 0 - 6 | Away | |
| Girl's Varsity Soccer | vs. Indian Mountain School | Nov 8 | 2:45 PM | Home | 1 - 4 | Home | |
| Varsity Cross Country | vs. Indian Mountain School | Nov 8 | 2:45 PM | Home | 58 - 38 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Nov 8 | 2:45 PM | Home | 5 - 0 | Home | |
| Varsity B Soccer | @ Indian Mountain School | Nov 8 | 2:45 PM | Indian Mountain School | 4 - 2 | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Nov 8 | 3:15 PM | Indian Mountain School | 2 - 3 | Away | |
| Varsity Volleyball | vs. Indian Mountain School | Nov 8 | 3:15 PM | Home | 3 - 1 | Home | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Dec 5 | 7:15 PM | Playing Fields - Lufkin Rink | 0 - 3 | Home | |
| Boy's Varsity Ice Hockey | vs. Westminster School | Dec 11 | 3:30 PM | Playing Fields - Lufkin Rink | 10 - 0 | Home | |
| Girl's Varsity Basketball | @ Sherman Middle School | Dec 11 | 3:45 PM | Sherman Middle School | 19 - 14 | Away | |
| Boy's Varsity Basketball | @ TBD | Dec 13 | 4:00 PM | Home | - | Away | Rescheduled to Dec 14 |
| Boy's Varsity Basketball | @ Avon Old Farms School | Dec 14 | 1:00 PM | Home | 36 - 43 | Away | |
| Girl's Varsity Basketball | vs. Ethel Walker School | Dec 14 | 2:30 PM | Home | 13 - 34 | Home | |
| Boy's Varsity Ice Hockey | @ Rectory School | Dec 14 | 4:30 PM | Rectory School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Dec 18 | 3:30 PM | Playing Fields - Lufkin Rink | 9 - 0 | Home | |
| Boy's Varsity B Basketball | vs. Mizzentop | Jan 8 | 4:00 PM | Home | 18 - 25 | Home | |
| Boy's Jr. Blue Basketball | @ Mizzentop | Jan 9 | 4:00 PM | Mizzentop / Patterson Recreation Center | 24 - 8 | Away | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 10 | 4:30 PM | Playing Fields - Lufkin Rink | 0 - 1 | Home | |
| Girl's Varsity Ice Hockey | @ Frederick Gunn School | Jan 10 | 4:30 PM | Frederick Gunn School | 10 - 1 | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 11 | 6:00 AM | Upland Country Day School | - | Away | |
| Boy's Varsity Ice Hockey | @ Team Philadelphia | Jan 11 | 12:00 PM | Upland Country Day School | 7 - 1 | Away | |
| Boy's Varsity Ice Hockey | @ Palmyra Black Knights | Jan 11 | 3:30 PM | Upland Country Day School | 0 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 12 | 8:30 AM | Upland Country Day School | 1 - 4 | Away | |
| Boy's Jr. Blue Basketball | vs. Dutchess Day School | Jan 14 | 3:30 PM | Home | 33 - 26 | Home | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Jan 14 | 4:15 PM | Home | 2 - 5 | Home | |
| Girl's Varsity Ice Hockey | @ Kent School | Jan 15 | 1:45 PM | Kent School | 5 - 1 | Away | |
| Boy's Varsity Ice Hockey | vs. Avon Old Farms School | Jan 15 | 2:30 PM | Playing Fields - Lufkin Rink | 0 - 2 | Home | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Jan 15 | 2:30 PM | Home | 55 - 62 | Home | |
| Varsity Ski Team | @ Dutchess Day School | Jan 15 | 3:00 PM | Mohawk Mountain Ski Area | 10 - 27 | Away | |
| Girl's Varsity Basketball | @ Kingswood-Oxford School | Jan 15 | 3:30 PM | Kingswood-Oxford School | 15 - 31 | Away | |
| Girl's Varsity B Basketball | vs. Berkshire Waldorf School | Jan 15 | 4:00 PM | Home | 14 - 23 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Jan 15 | 4:15 PM | Playing Fields - Lufkin Rink | 5 - 1 | Home | |
| Boy's Varsity Basketball | @ Oakwood Friends School | Jan 16 | 3:30 PM | Oakwood Friends School | 49 - 25 | Away | |
| Boy's Varsity B Basketball | @ Sherman Middle School | Jan 16 | 3:45 PM | Sherman Middle School | 26 - 29 | Away | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Jan 17 | 3:15 PM | Indian Mountain School | 38 - 21 | Away | |
| Varsity B Ice Hockey | @ Eaglebrook School | Jan 17 | 4:00 PM | Eaglebrook School | 1 - 3 | Away | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Jan 17 | 4:15 PM | Playing Fields - Lufkin Rink | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | @ Choate Rosemary Hall | Jan 17 | 4:45 PM | Choate Rosemary Hall | 6 - 0 | Away | |
| Girl's Varsity Basketball | vs. Choate Rosemary Hall | Jan 18 | 2:30 PM | Home | 17 - 41 | Home | |
| Boy's Varsity Ice Hockey | @ Rectory School | Jan 21 | 2:10 PM | Pomfret School | 0 - 7 | Away | |
| Girl's Varsity B Basketball | vs. Renbrook School | Jan 21 | 3:45 PM | Home | 15 - 23 | Home | |
| Boy's Varsity B Basketball | vs. Trinity Pawling School | Jan 21 | 4:00 PM | Home | 39 - 49 | Home | |
| Boy's Varsity Basketball | vs. Canterbury School | Jan 22 | 2:30 PM | Home | 59 - 43 | Home | |
| Varsity Ski Team | @ Dutchess Day School | Jan 22 | 3:00 PM | Catamount Ski Area | 8 - 33 | Away | |
| Girl's Varsity Basketball | vs. Indian Mountain School | Jan 22 | 4:00 PM | Home | 26 - 11 | Home | |
| Girl's Varsity Ice Hockey | @ Millbrook School | Jan 22 | 4:45 PM | Millbrook School | 10 - 1 | Away | |
| Boy's Varsity Ice Hockey | vs. Fairfield Country Day | Jan 23 | 2:45 PM | Playing Fields - Lufkin Rink | 0 - 7 | Home | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Jan 23 | 3:30 PM | Washington Montessori School (WMS) | 35 - 11 | Away | |
| Winter Volleyball | @ Dutchess Day School | Jan 23 | 3:45 PM | Dutchess Day School | 3 - 0 | Away | |
| Boy's Varsity B Basketball | vs. Maplebrook School | Jan 24 | 3:30 PM | Home | 52 - 31 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Jan 24 | 3:30 PM | Catamount Ski Area | - | Away | |
| Boy's Varsity Basketball | vs. Brunswick School | Jan 24 | 4:00 PM | Home | 46 - 47 | Home | |
| Girl's Varsity Basketball | @ Frederick Gunn School | Jan 24 | 4:30 PM | Frederick Gunn School | 32 - 13 | Away | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 24 | 4:30 PM | Playing Fields - Lufkin Rink | 2 - 3 | Home | |
| Girl's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 25 | 6:00 AM | Upland Country Day School | - | Away | |
| Girl's Varsity Ice Hockey | @ Upland Country Day School | Jan 25 | 12:00 PM | Upland Country Day School | 2 - 7 | Away | |
| Boy's Varsity Ice Hockey | @ Vermont Flames | Jan 25 | 1:00 PM | Cardigan Mountain School | 1 - 5 | Away | |
| Girl's Varsity Ice Hockey | @ Lower Merion Girls Hockey | Jan 25 | 2:30 PM | Upland Country Day School | 7 - 0 | Away | |
| Girl's Varsity Ice Hockey | @ Union Thunder Girls Ice Hockey | Jan 25 | 6:30 PM | Upland Country Day School | 3 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 25 | 6:30 PM | Cardigan Mountain School | 4 - 0 | Away | |
| Girl's Varsity Ice Hockey | @ Lower Merion Girls Hockey | Jan 26 | 8:00 AM | Upland Country Day School | 7 - 1 | Away | |
| Girl's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 26 | 8:00 AM | Upland Country Day School | - | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 26 | 9:00 AM | Cardigan Mountain School | 4 - 0 | Away | |
| Boy's Varsity B Basketball | @ Berkshire Waldorf School | Jan 27 | 3:45 PM | Kilpatrick Athletic Center | 18 - 26 | Away | |
| Boy's Varsity B Basketball | vs. Sherman Middle School | Jan 28 | 3:45 PM | Home | 30 - 32 | Home | |
| Girl's Varsity Basketball | vs. Canterbury School | Jan 29 | 2:30 PM | Home | 28 - 20 | Home | |
| Boy's Varsity Ice Hockey | vs. Berkshire School | Jan 29 | 2:30 PM | Playing Fields - Lufkin Rink | 4 - 3 | Home | |
| Varsity Ski Team | @ Dutchess Day School | Jan 29 | 3:00 PM | Mohawk Mountain Ski Area | 12 - 32 | Away | |
| Girl's Varsity B Basketball | @ Indian Mountain School | Jan 29 | 3:15 PM | Indian Mountain School | 14 - 8 | Away | |
| Boy's Jr. Blue Basketball | @ Renbrook School | Jan 29 | 3:30 PM | Renbrook School | 36 - 32 | Away | |
| Boy's Varsity B Basketball | @ TBD | Jan 29 | 3:45 PM | Home | - | Away | Rescheduled to Jan 27 |
| Boy's Varsity Basketball | vs. Avon Old Farms School | Jan 29 | 4:00 PM | Home | 55 - 43 | Home | |
| Girl's Varsity Ice Hockey | vs. Canterbury School | Jan 29 | 4:15 PM | Playing Fields - Lufkin Rink | 6 - 1 | Home | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Jan 30 | 3:30 PM | Washington Montessori School (WMS) | 6 - 35 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Jan 30 | 3:45 PM | Home | 2 - 1 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Jan 31 | 3:00 PM | Playing Fields - Lufkin Rink | 1 - 1 | Home | |
| Boy's Varsity Basketball | vs. Indian Mountain School | Jan 31 | 3:15 PM | Home | 44 - 68 | Home | |
| Girl's Varsity Basketball | @ Choate Rosemary Hall | Jan 31 | 4:00 PM | Home | 26 - 15 | Away | |
| Girl's Varsity Ice Hockey | vs. Kent School | Feb 1 | 2:30 PM | Playing Fields - Lufkin Rink | 6 - 2 | Home | |
| Boy's Varsity Ice Hockey | @ Brunswick School | Feb 3 | 4:00 PM | Brunswick School - Hartong Rink | 4 - 2 | Away | |
| Boy's Varsity Basketball | @ Trinity Pawling School | Feb 3 | 4:00 PM | Trinity Pawling School | 50 - 58 | Away | |
| Girl's Varsity B Basketball | vs. Sherman Middle School | Feb 4 | 3:45 PM | Home | 7 - 28 | Home | |
| Boy's Varsity Ice Hockey | @ Taft School | Feb 5 | 2:30 PM | Taft School | 10 - 3 | Away | |
| Varsity Ski Team | @ Washington Montessori School (WMS) | Feb 5 | 3:00 PM | Mohawk Mountain Ski Area | 3 - 18 | Away | |
| Girl's Varsity Basketball | @ Hotchkiss School | Feb 5 | 3:15 PM | Hotchkiss School | 45 - 15 | Away | |
| Boy's Varsity Basketball | vs. Taft School | Feb 5 | 3:15 PM | Home | 47 - 40 | Home | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Feb 5 | 3:15 PM | Playing Fields - Lufkin Rink | 4 - 0 | Home | |
| Boy's Varsity B Basketball | @ Hopkins School | Feb 5 | 3:45 PM | Hopkins School | 17 - 43 | Away | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Feb 6 | 3:30 PM | Washington Montessori School (WMS) | - | Away | Cancelled |
| Winter Volleyball | vs. Dutchess Day School | Feb 6 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity B Basketball | @ Renbrook School | Feb 6 | 4:00 PM | Renbrook School | - | Away | Cancelled |
| Girl's Varsity Ice Hockey | vs. Taft School | Feb 6 | 4:00 PM | Playing Fields - Lufkin Rink | - | Home | Cancelled |
| Varsity B Ice Hockey | @ TBD | Feb 7 | 3:00 PM | Home | - | Away | Rescheduled to Feb 14 |
| Boy's Varsity Basketball | @ Indian Mountain School | Feb 7 | 3:00 PM | Indian Mountain School | 32 - 62 | Away | |
| Boy's Varsity B Basketball | vs. Indian Mountain School | Feb 7 | 3:15 PM | Home | 22 - 32 | Home | |
| Boy's Varsity B Basketball | @ Maplebrook School Boys Basketball Tournament | Feb 8 | 11:00 AM | Maplebrook School | - | Away | |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Feb 12 | 3:00 PM | Home | 36 - 22 | Home | |
| Varsity Ski Team | @ Dutchess Day School | Feb 12 | 3:00 PM | Catamount Ski Area | 7 - 40 | Away | |
| Girl's Varsity Ice Hockey | @ Hotchkiss School | Feb 12 | 3:00 PM | Hotchkiss School | 2 - 0 | Away | |
| Girl's Varsity B Basketball | @ Berkshire Waldorf School | Feb 12 | 3:45 PM | Kilpatrick Athletic Center | 6 - 27 | Away | |
| Boy's Varsity B Basketball | vs. Berkshire Waldorf School | Feb 12 | 4:00 PM | Home | 42 - 40 | Home | |
| Boy's Varsity B Basketball | vs. Oakwood Friends School | Feb 13 | 3:30 PM | Home | 42 - 21 | Home | |
| Boy's Varsity Ice Hockey | @ Fairfield Country Day | Feb 13 | 3:30 PM | Wonderland of Ice | - | Away | |
| Winter Volleyball | @ Dutchess Day School | Feb 13 | 3:45 PM | Dutchess Day School | 2 - 1 | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 14 | 3:00 PM | Home | 2 - 4 | Home | |
| Boy's Varsity Basketball | vs. Salisbury School | Feb 14 | 4:00 PM | Home | 47 - 37 | Home | |
| Girl's Varsity Ice Hockey | @ Berkshire School | Feb 14 | 4:45 PM | Berkshire School | 6 - 1 | Away | |
| Boy's Varsity Ice Hockey | @ Avon Old Farms School | Feb 14 | 5:25 PM | Avon Old Farms School | 6 - 1 | Away | |
| Girl's Varsity Basketball | vs. Hotchkiss School | Feb 14 | 5:30 PM | Home | 28 - 16 | Home | |
| Girl's Varsity Ice Hockey | vs. Philadelphia Jr. Flyers | Feb 15 | 12:00 PM | Playing Fields - Lufkin Rink | 1 - 4 | Home | |
| Girl's Varsity Basketball | @ Canterbury School | Feb 15 | 1:30 PM | Canterbury School | - | Away | Cancelled |
| Girl's Varsity Ice Hockey | vs. Westminster School | Feb 15 | 2:30 PM | Playing Fields - Lufkin Rink | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | @ Brunswick School | Feb 18 | 4:00 PM | Brunswick School - Hartong Rink | 5 - 7 | Away | |
| Boy's Varsity B Basketball | @ Trinity Pawling School | Feb 18 | 4:00 PM | Trinity Pawling School | 32 - 52 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 19 | 10:30 AM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | @ Indian Mountain School | Feb 19 | 3:15 PM | Indian Mountain School | 26 - 14 | Away | |
| Boy's Varsity Basketball | vs. Hopkins School | Feb 19 | 3:30 PM | Home | 57 - 35 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 19 | 4:15 PM | Playing Fields - Lufkin Rink | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | vs. Indian Mountain School | Feb 19 | 4:15 PM | Home | 1 - 3 | Home | |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Feb 20 | 3:00 PM | Washington Montessori School (WMS) | 32 - 23 | Home | |
| Girl's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 20 | 3:30 PM | Home | 22 - 39 | Home | |
| Winter Volleyball | @ Dutchess Day School | Feb 20 | 3:45 PM | Dutchess Day School | 3 - 0 | Away | |
| Boy's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 20 | 4:15 PM | Home | 58 - 27 | Home | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Feb 21 | 3:00 PM | Indian Mountain School | 55 - 19 | Away | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Feb 21 | 4:15 PM | Home | 65 - 24 | Home | |
| Girl's Varsity Basketball | vs. Frederick Gunn School | Feb 21 | 4:30 PM | Home | 30 - 12 | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 22 | 10:30 AM | Home | - | Home | |
| Boy's Varsity Ice Hockey | vs. Cardigan Mountain School | Feb 22 | 12:00 PM | Home | 2 - 2 | Home | |
| Boy's Varsity Basketball | @ Westminster School | Feb 22 | 2:30 PM | Westminster School | 33 - 44 | Away | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Feb 22 | 4:30 PM | Home | 2 - 5 | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 23 | 8:00 AM | Playing Fields - Lufkin Rink | - | Home | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Feb 23 | 10:30 AM | Home | 4 - 1 | Home | |
| Boy's Varsity Basketball | @ Canterbury School | Feb 24 | 4:15 PM | Canterbury School | 58 - 55 | Away | |
| Girl's Varsity Ice Hockey | vs. Berkshire School | Feb 24 | 4:30 PM | Playing Fields - Lufkin Rink | 5 - 1 | Home | |
| Girl's Varsity B Basketball | @ Ethel Walker School | Feb 25 | 4:15 PM | Ethel Walker School | - | Away | |
| Boy's Varsity Ice Hockey | vs. Salisbury School | Feb 26 | 2:30 PM | Playing Fields - Lufkin Rink | 3 - 4 | Home | |
| Girl's Varsity Basketball | vs. Choate Rosemary Hall | Feb 26 | 3:30 PM | Home | 27 - 9 | Home | |
| Boy's Varsity Basketball | vs. Berkshire School | Feb 26 | 3:30 PM | Home | 59 - 53 | Home | |
| Boy's Jr. Blue Basketball | @ Dutchess Day School | Feb 26 | 4:00 PM | Dutchess Day School | 45 - 17 | Away | |
| Boy's Varsity B Basketball | @ Indian Mountain School | Feb 26 | 4:15 PM | Indian Mountain School | 32 - 34 | Away | |
| Girl's Varsity Ice Hockey | vs. Frederick Gunn School | Feb 26 | 4:15 PM | Playing Fields - Lufkin Rink | 5 - 1 | Home | |
| Boy's Jr. Blue Basketball | vs. Renbrook School | Feb 27 | 3:45 PM | Home | 32 - 24 | Home | |
| Winter Volleyball | vs. Dutchess Day School | Feb 27 | 3:45 PM | Home | 2 - 1 | Home | |
| Varsity B Ice Hockey | @ Indian Mountain School | Feb 28 | 3:00 PM | Hotchkiss School | 4 - 4 | Away | |
| Girl's Varsity B Basketball | vs. Indian Mountain School | Feb 28 | 3:15 PM | Home | 21 - 8 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Feb 28 | 3:30 PM | Catamount Ski Area | - | Away | |
| Girl's Varsity Basketball | @ Berkshire School | Feb 28 | 4:30 PM | Berkshire School | 41 - 13 | Away | |
| Girl's Varsity Ice Hockey | vs. Union Thunder Girls Ice Hockey | Feb 28 | 7:00 PM | Home | 1 - 0 | Home | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Mar 1 | 9:15 AM | Home | 1 - 6 | Home | |
| Girl's Varsity Ice Hockey | vs. Hat Tricks | Mar 1 | 1:30 PM | Home | 0 - 1 | Home | |
| Boy's Varsity Lacrosse | vs. Hamden Hall | Apr 8 | 4:00 PM | Home | 12 - 2 | Home | |
| Varsity Softball | @ Westminster School | Apr 8 | 4:00 PM | Home | - | Away | Cancelled |
| Varsity A Tennis | vs. Millbrook School | Apr 8 | 4:15 PM | Home | - | Home | Cancelled |
| Varsity Softball | @ TBD | Apr 9 | 3:15 PM | Home | - | Away | Rescheduled to Apr 8 |
| Girl's Varsity Lacrosse | @ Renbrook School | Apr 9 | 3:15 PM | Renbrook School | 6 - 6 | Away | |
| Varsity Baseball | @ Berkshire School | Apr 9 | 3:15 PM | Berkshire School | - | Away | Cancelled |
| Boy's Varsity B Lacrosse | vs. Dutchess Day School | Apr 10 | 3:45 PM | Home | 1 - 8 | Home | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | Apr 11 | 3:15 PM | Home | 1 - 8 | Home | |
| Varsity B Tennis | vs. Indian Mountain School | Apr 11 | 3:15 PM | Home | 5 - 4 | Home | |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | Apr 11 | 3:30 PM | Indian Mountain School | 9 - 8 | Away | |
| Varsity Baseball | @ Oakwood Friends School | Apr 11 | 3:45 PM | Oakwood Friends School | 15 - 0 | Away | |
| Girl's Varsity Lacrosse | @ TBD | Apr 11 | 4:00 PM | Home | - | Away | Rescheduled to May 6 |
| Boy's Varsity Lacrosse | vs. Eaglebrook School | Apr 12 | 2:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity Lacrosse | vs. TBD | Apr 14 | 4:30 PM | Home | - | Home | Rescheduled to Apr 21 |
| Varsity B Baseball | @ Renbrook School | Apr 15 | 3:45 PM | Renbrook School | 3 - 14 | Away | |
| Varsity Softball | vs. Hamden Hall | Apr 15 | 4:00 PM | Home | 15 - 10 | Home | |
| Boy's Varsity B Lacrosse | vs. Trinity Pawling School | Apr 15 | 4:00 PM | Home | 0 - 9 | Home | |
| Varsity B Tennis | vs. Renbrook School | Apr 15 | 4:00 PM | Home | 8 - 0 | Home | |
| Girl's Varsity B Lacrosse | @ Ethel Walker School | Apr 15 | 4:30 PM | Ethel Walker School | - | Away | |
| Varsity A Tennis | @ Taft School | Apr 16 | 2:30 PM | Taft School | 7 - 0 | Away | |
| Girl's Varsity Lacrosse | @ Berkshire School | Apr 16 | 3:15 PM | Berkshire School | 9 - 3 | Away | |
| Varsity Baseball | vs. Berkshire School | Apr 16 | 3:15 PM | Home | 11 - 1 | Home | |
| Girl's Varsity B Lacrosse | vs. Dutchess Day School | Apr 16 | 3:45 PM | Home | 3 - 11 | Home | |
| Boy's Varsity Lacrosse | vs. Rectory School | Apr 16 | 4:00 PM | Avon Old Farms School | 7 - 6 | Home | |
| Varsity Softball | vs. Renbrook School | Apr 17 | 3:45 PM | Home | 10 - 9 | Home | |
| Boy's Varsity B Lacrosse | @ Dutchess Day School | Apr 17 | 4:00 PM | Dutchess Day School | 2 - 10 | Away | |
| Varsity B Tennis | @ Indian Mountain School | Apr 18 | 3:00 PM | Indian Mountain School | 5 - 3 | Away | |
| Varsity Baseball | @ Trinity Pawling School | Apr 18 | 3:45 PM | Trinity Pawling School | 9 - 14 | Away | |
| Varsity A Tennis | @ Hotchkiss School | Apr 18 | 4:30 PM | Hotchkiss School | 3 - 4 | Away | |
| Girl's Varsity Lacrosse | vs. Hotchkiss School | Apr 18 | 4:45 PM | Home | 6 - 8 | Home | |
| Boy's Varsity Lacrosse | vs. Hamden Hall | Apr 21 | 4:30 PM | Home | 2 - 7 | Home | |
| Varsity Baseball | @ Canterbury School | Apr 22 | 4:00 PM | Canterbury School | 2 - 8 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | Apr 22 | 4:00 PM | Home | 1 - 8 | Home | |
| Varsity B Tennis | @ Dutchess Day School | Apr 22 | 4:00 PM | Dutchess Day School | 4 - 3 | Away | |
| Girl's Varsity Lacrosse | @ Indian Mountain School | Apr 23 | 3:00 PM | Indian Mountain School | 11 - 6 | Away | |
| Varsity A Tennis | vs. Hotchkiss School | Apr 23 | 3:15 PM | Home | 5 - 2 | Home | |
| Varsity Softball | @ Indian Mountain School | Apr 23 | 3:15 PM | Indian Mountain School | 17 - 9 | Away | |
| Boy's Varsity Lacrosse | @ Hopkins School | Apr 23 | 3:30 PM | Hopkins School | 13 - 4 | Away | |
| Varsity Crew | @ Salisbury School | Apr 23 | 3:30 PM | Salisbury School | - | Away | |
| Boy's Varsity B Lacrosse | vs. Dutchess Day School | Apr 23 | 3:45 PM | Home | 1 - 9 | Home | |
| Varsity B Baseball | vs. Masters School (CT) | Apr 23 | 4:00 PM | Home | 10 - 5 | Home | |
| Varsity Baseball | vs. Indian Mountain School | Apr 25 | 3:15 PM | Home | 8 - 7 | Home | |
| Varsity B Tennis | @ Indian Mountain School | Apr 25 | 3:15 PM | Indian Mountain School | 4 - 5 | Away | |
| Girl's Varsity B Lacrosse | @ Dutchess Day School | Apr 25 | 3:45 PM | Home | 3 - 6 | Away | |
| Varsity Softball | vs. Sherman Middle School | Apr 25 | 3:45 PM | Home | 19 - 11 | Home | |
| Varsity A Tennis | vs. Berkshire School | Apr 25 | 4:15 PM | Home | 7 - 0 | Home | |
| Girl's Varsity Lacrosse | vs. Loomis Chaffee | Apr 25 | 4:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity Lacrosse | @ Eaglebrook School | Apr 25 | 4:30 PM | Eaglebrook School | 5 - 6 | Away | |
| Boy's Varsity Lacrosse | @ Hamden Hall | Apr 29 | 4:00 PM | Hamden Hall | 10 - 2 | Away | |
| Varsity A Tennis | @ Indian Mountain School | Apr 29 | 4:00 PM | Indian Mountain School | 7 - 0 | Away | |
| Varsity B Baseball | @ Indian Mountain School | Apr 29 | 4:00 PM | Indian Mountain School | 9 - 1 | Away | |
| Varsity B Tennis | vs. Hamden Hall | Apr 29 | 4:00 PM | Home | 7 - 0 | Home | |
| Varsity Crew | @ Hotchkiss School | Apr 30 | 3:00 PM | Hotchkiss School | - | Away | Cancelled |
| Girl's Varsity Lacrosse | vs. Millbrook School | Apr 30 | 3:30 PM | Home | 8 - 3 | Home | |
| Varsity Baseball | vs. Brunswick School | Apr 30 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity Softball | @ Sherman Middle School | Apr 30 | 3:45 PM | Softball Field Location -43 CT-39, Sherman, CT 06784 | 9 - 16 | Away | |
| Boy's Varsity Lacrosse | vs. Brunswick School | May 1 | 3:45 PM | Home | 1 - 12 | Home | |
| Varsity B Tennis | @ Washington Montessori School (WMS) | May 1 | 3:45 PM | Washington Montessori School (WMS) | 9 - 0 | Away | |
| Boy's Varsity B Lacrosse | @ Renbrook School | May 1 | 4:00 PM | Renbrook School | 5 - 1 | Away | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | May 2 | 3:15 PM | Indian Mountain School | 0 - 7 | Away | |
| Varsity B Baseball | @ Kent Center School | May 2 | 3:30 PM | Kent Center School | 5 - 6 | Away | |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | May 2 | 3:30 PM | Indian Mountain School | 8 - 4 | Away | |
| Varsity B Tennis | vs. Mizzentop | May 2 | 3:45 PM | Home | 9 - 0 | Home | |
| Varsity Softball | vs. Westminster School | May 2 | 4:20 PM | Home | 14 - 8 | Home | |
| Varsity Crew | @ Choate Rosemary Hall | May 2 | 4:30 PM | Choate Rosemary Hall | - | Away | |
| Varsity Softball | vs. TBD | May 3 | 2:30 PM | Home | - | Home | Rescheduled to May 2 |
| Varsity A Tennis | vs. Trinity Pawling School | May 3 | 2:30 PM | Home | 7 - 0 | Home | |
| Varsity Baseball | vs. Canterbury School | May 3 | 2:30 PM | Home | - | Home | |
| Girl's Varsity Lacrosse | vs. Westminster School | May 3 | 2:30 PM | Home | 8 - 3 | Home | |
| Boy's Varsity Lacrosse | vs. Indian Mountain School | May 3 | 2:30 PM | Home | 1 - 8 | Home | |
| Varsity Crew | @ Founder's Day Regatta | May 4 | 7:00 AM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity A Tennis | vs. Renbrook School | May 6 | 3:45 PM | Home | 8 - 1 | Home | |
| Varsity Softball | @ Hamden Hall | May 6 | 4:00 PM | Hamden Hall | - | Away | Cancelled |
| Girl's Varsity Lacrosse | @ Kent School | May 6 | 4:00 PM | Home | - | Away | Cancelled |
| Boy's Varsity Lacrosse | @ Brunswick School | May 6 | 4:00 PM | Brunswick School King Street Campus (1252 King St.) | - | Away | Cancelled |
| Girl's Varsity Lacrosse | vs. Frederick Gunn School | May 7 | 2:00 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 9 - 0 | Home | |
| Varsity Baseball | @ Salisbury School | May 7 | 3:15 PM | Salisbury School | 2 - 6 | Away | |
| Varsity B Baseball | vs. Indian Mountain School | May 7 | 3:15 PM | Home | 12 - 0 | Home | |
| Varsity B Tennis | vs. Westminster School | May 7 | 3:15 PM | Home | 6 - 3 | Home | |
| Varsity Crew | @ Berkshire School | May 7 | 3:30 PM | Camp Sloane | - | Away | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | May 7 | 3:30 PM | Home | 3 - 3 | Home | |
| Boy's Varsity Lacrosse | vs. Renbrook School | May 8 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity B Baseball | vs. Kent Center School | May 9 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity A Tennis | vs. Frederick Gunn School | May 9 | 3:45 PM | Home | 8 - 1 | Home | |
| Varsity Baseball | vs. Frederick Gunn School | May 9 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity B Lacrosse | vs. Berkshire Waldorf School | May 9 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity Lacrosse | vs. Rumsey Hall Girls Lacrosse Invitational | May 10 | 8:00 AM | Home | - | Home | Cancelled |
| Varsity Crew | @ Litchfield Hills Rowing Club | May 10 | 10:30 AM | Litchfield Hills Rowing Club - Boathouse | - | Away | Cancelled |
| Varsity B Tennis | vs. Washington Montessori School (WMS) | May 12 | 3:00 PM | Home | 7 - 0 | Home | |
| Varsity B Tennis | vs. Dutchess Day School | May 13 | 3:45 PM | Home | 8 - 0 | Home | |
| Varsity A Tennis | @ Choate Rosemary Hall | May 13 | 4:00 PM | Choate Rosemary Hall | 4 - 3 | Away | |
| Girl's Varsity Lacrosse | vs. Indian Mountain School | May 13 | 4:00 PM | Home | 10 - 7 | Home | |
| Boy's Varsity B Lacrosse | @ Trinity Pawling School | May 13 | 4:00 PM | Trinity Pawling School | 1 - 6 | Away | |
| Boy's Varsity Lacrosse | @ Westminster School | May 13 | 4:00 PM | Home | - | Away | Cancelled |
| Varsity Crew | vs. Lower Boat Regatta | May 14 | 3:00 PM | Lake Waramaug - RHS Crew Home | - | Home | |
| Varsity A Tennis | vs. Kent School | May 14 | 3:15 PM | Home | 9 - 0 | Home | |
| Varsity Softball | vs. Indian Mountain School | May 14 | 3:15 PM | Home | - | Home | |
| Varsity Baseball | @ Kent School | May 14 | 3:15 PM | Kent School | - | Away | Cancelled |
| Boy's Varsity Lacrosse | vs. Hopkins School | May 14 | 3:30 PM | Home | 9 - 6 | Home | |
| Varsity B Baseball | @ Berkshire Waldorf School | May 14 | 3:45 PM | Berkshire Waldorf School | 6 - 12 | Away | |
| Girl's Varsity B Lacrosse | vs. Berkshire Waldorf School | May 14 | 3:45 PM | Home | 7 - 4 | Home | |
| Girl's Varsity Lacrosse | @ Canterbury School | May 14 | 4:30 PM | Canterbury School | 7 - 0 | Away | |
| Boy's Varsity B Lacrosse | vs. Renbrook School | May 15 | 3:45 PM | Home | 3 - 1 | Home | |
| Varsity B Baseball | vs. Renbrook School | May 15 | 3:45 PM | Home | 4 - 9 | Home | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | May 15 | 4:30 PM | Home | - | Home | Cancelled |
| Varsity B Tennis | @ TBD | May 16 | 3:45 PM | Mizzentop | - | Away | Cancelled |
| Girl's Varsity Lacrosse | vs. Taft School | May 19 | 4:00 PM | Home | 9 - 0 | Home | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | May 20 | 4:00 PM | Indian Mountain School | 3 - 6 | Away | |
| Varsity B Baseball | @ Masters School (CT) | May 20 | 4:00 PM | Home | 10 - 6 | Away | |
| Varsity Softball | @ Rectory School | May 20 | 4:00 PM | Ethel Walker School | 13 - 14 | Away | |
| Varsity A Tennis | vs. Indian Mountain School | May 20 | 4:00 PM | Home | 9 - 0 | Home | |
| Girl's Varsity B Lacrosse | @ Dutchess Day School | May 20 | 4:00 PM | Dutchess Day School | 6 - 9 | Away | |
| Varsity Baseball | vs. Avon Old Farms School | May 20 | 4:30 PM | Home | 8 - 10 | Home | |
| Varsity Softball | @ Indian Mountain School | May 21 | 2:45 PM | Indian Mountain School | 12 - 16 | Away | |
| Varsity Baseball | @ Indian Mountain School | May 21 | 3:00 PM | Indian Mountain School | 8 - 1 | Away | |
| Boy's Varsity Lacrosse | @ Indian Mountain School | May 21 | 3:15 PM | Indian Mountain School | 2 - 11 | Away | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | May 21 | 3:15 PM | Home | 1 - 6 | Home | |
| Varsity B Tennis | vs. Indian Mountain School | May 21 | 3:15 PM | Home | 7 - 2 | Home | |
| Varsity A Tennis | @ Salisbury School | May 21 | 3:30 PM | Salisbury School | - | Away | Cancelled |
| Varsity B Baseball | vs. Berkshire Waldorf School | May 21 | 4:00 PM | Home | 2 - 2 | Home | |
| Girl's Varsity Lacrosse | @ Rectory School | May 21 | 4:00 PM | Ethel Walker School | 8 - 1 | Away | |
| No events found. | |||||||
| Team | Opponent | Date | Time | Location | Result | Advantage | Status |
|---|---|---|---|---|---|---|---|
| Boy's Varsity Soccer | vs. Trinity Pawling School | Sep 19 | 4:00 PM | Seibert Memorial Field - Siebert Field - 2900 | 4 - 0 | Home | |
| Varsity Volleyball | @ Miss Porter's School | Sep 20 | 3:00 PM | Miss Porter's School | 3 - 0 | Away | |
| Varsity Field Hockey | vs. Westminster School | Sep 20 | 3:15 PM | Home | 4 - 0 | Home | |
| Blue Dog Bikes - Racing Team | @ Kent School | Sep 20 | 3:30 PM | Kent School | - | Away | |
| Varsity B Volleyball | vs. Oakwood Friends School | Sep 20 | 3:30 PM | Home | 1 - 2 | Home | |
| Girl's Varsity Soccer | @ Renbrook School | Sep 20 | 3:30 PM | Renbrook School | 1 - 5 | Away | |
| Varsity Cross Country | @ Rhino Run - Taft School Invitational | Sep 20 | 4:00 PM | Taft School | - | Away | |
| Junior Blue Soccer | @ Washington Montessori School (WMS) | Sep 21 | 3:45 PM | Washington Montessori School (WMS) | 11 - 7 | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Sep 22 | 3:15 PM | Indian Mountain School | 2 - 1 | Away | |
| Varsity Volleyball | @ Berkshire School | Sep 22 | 3:30 PM | Berkshire School | 3 - 2 | Away | |
| Junior Blue Soccer | vs. Indian Mountain School | Sep 22 | 3:30 PM | Home | 10 - 5 | Home | |
| Varsity B Soccer | @ Mizzentop | Sep 22 | 3:45 PM | Mizzentop | 1 - 7 | Away | |
| Boy's Varsity Soccer | vs. Taft School | Sep 22 | 4:15 PM | Home | 0 - 4 | Home | |
| Girl's Varsity Soccer | vs. Millbrook School | Sep 22 | 4:30 PM | Home | - | Home | Cancelled |
| Varsity Football | @ Williston Jamboree | Sep 23 | 10:00 AM | Williston Northampton School | - | Away | |
| Girl's Varsity Soccer | vs. Canterbury School | Sep 23 | 2:30 PM | Home | 7 - 4 | Home | |
| Varsity B Volleyball | vs. Miss Porter's School | Sep 27 | 3:00 PM | Home | 0 - 2 | Home | |
| Boy's Varsity Soccer | vs. Avon Old Farms School | Sep 27 | 3:15 PM | Home | 10 - 0 | Home | |
| Varsity Field Hockey | vs. Berkshire School | Sep 27 | 3:15 PM | Home | 2 - 0 | Home | |
| Blue Dog Bikes - Racing Team | @ Indian Mountain School | Sep 27 | 3:30 PM | Indian Mountain School | - | Away | |
| Varsity Cross Country | vs. Washington Montessori School (WMS) | Sep 27 | 3:30 PM | Home | 15 - 70 | Home | |
| Varsity Volleyball | @ Choate Rosemary Hall | Sep 27 | 3:30 PM | Choate Rosemary Hall | 2 - 0 | Away | |
| Varsity B Field Hockey | @ Mizzentop | Sep 27 | 3:45 PM | Mizzentop | 0 - 0 | Away | |
| Varsity B Soccer | @ Renbrook School | Sep 28 | 4:00 PM | Renbrook School | 0 - 7 | Away | |
| Varsity Football | @ Avon Old Farms School | Sep 29 | 3:00 PM | Avon Old Farms School | 22 - 7 | Away | |
| Varsity Volleyball | @ Rectory School | Sep 29 | 3:00 PM | Ethel Walker School | 2 - 0 | Away | |
| Varsity Cross Country | @ Indian Mountain School | Sep 29 | 3:30 PM | Indian Mountain School | - | Away | Cancelled |
| Girl's Varsity Soccer | vs. Sherman Middle School | Sep 29 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity B Soccer | @ Dutchess Day Soccer Tournament 7 v.7 | Sep 29 | 3:30 PM | Dutchess Day School | - | Away | Cancelled |
| Junior Blue Soccer | @ Dutchess Day School | Sep 29 | 3:30 PM | Dutchess Day School | - | Away | Cancelled |
| Boy's Varsity Soccer | @ Frederick Gunn School | Sep 29 | 4:00 PM | Frederick Gunn School | - | Away | Cancelled |
| Varsity Field Hockey | vs. Frederick Gunn School | Sep 29 | 4:15 PM | Playing Fields - Cornell Athletic Field | - | Home | Cancelled |
| Varsity Field Hockey | vs. Miss Porter's School | Sep 30 | 12:00 PM | Home | - | Home | Cancelled |
| Varsity B Soccer | vs. TBD | Oct 3 | 3:30 PM | Home | - | Home | Rescheduled to Oct 4 |
| Junior Blue Soccer | vs. Dutchess Day School | Oct 3 | 3:45 PM | Home | 8 - 2 | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 3 | 3:45 PM | Home | 0 - 1 | Home | |
| Varsity B Volleyball | @ Oakwood Friends School | Oct 3 | 4:00 PM | Oakwood Friends School | 3 - 0 | Away | |
| Varsity Volleyball | vs. Kent School | Oct 4 | 3:00 PM | Home | 3 - 0 | Home | |
| Varsity Football | @ Fessenden School | Oct 4 | 3:00 PM | Suffield Academy | 0 - 30 | Away | |
| Girl's Varsity Soccer | @ Canterbury School | Oct 4 | 3:15 PM | Canterbury School | 4 - 3 | Away | |
| Boy's Varsity Soccer | @ Hotchkiss School | Oct 4 | 3:15 PM | Hotchkiss School | 5 - 6 | Away | |
| Varsity B Soccer | vs. Sherman Middle School | Oct 4 | 3:30 PM | Home | 2 - 3 | Home | |
| Blue Dog Bikes - Racing Team | @ Hotchkiss School | Oct 4 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity Cross Country | vs. Indian Mountain School | Oct 4 | 3:45 PM | Home | 33 - 24 | Home | |
| Varsity Field Hockey | @ Canterbury School | Oct 4 | 4:00 PM | Canterbury School | 4 - 1 | Away | |
| Junior Blue Soccer | @ Mizzentop | Oct 6 | 3:45 PM | Mizzentop | - | Away | Cancelled |
| Varsity B Soccer | vs. Mizzentop | Oct 6 | 4:00 PM | Home | 0 - 0 | Home | |
| Boy's Varsity Soccer | @ Millbrook School | Oct 6 | 4:00 PM | Millbrook School | 4 - 3 | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Oct 6 | 4:00 PM | Home | 2 - 1 | Home | |
| Varsity Field Hockey | @ Loomis Chaffee | Oct 6 | 4:15 PM | Loomis Chaffee | - | Away | Cancelled |
| Varsity Field Hockey | vs. Frederick Gunn School | Oct 6 | 4:15 PM | Home | 7 - 0 | Home | |
| Varsity Volleyball | @ Hopkins School | Oct 6 | 4:30 PM | Hopkins School | 3 - 0 | Away | |
| Girl's Varsity Soccer | @ Miss Porter's School | Oct 7 | 12:00 PM | Miss Porter's School | 3 - 3 | Away | |
| Varsity Football | @ Hopkins School | Oct 9 | 4:15 PM | Home | 38 - 12 | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 10 | 4:00 PM | Dutchess Day School | 1 - 0 | Away | |
| Varsity B Soccer | @ Dutchess Day School | Oct 10 | 4:00 PM | Dutchess Day School | 3 - 4 | Away | |
| Varsity Volleyball | @ Kent School | Oct 10 | 4:15 PM | Kent School | 3 - 1 | Away | |
| Girl's Varsity Soccer | vs. Miss Porter's School | Oct 11 | 3:00 PM | Home | 7 - 0 | Home | |
| Boy's Varsity Soccer | vs. Kent School | Oct 11 | 3:15 PM | Home | 6 - 0 | Home | |
| Varsity Volleyball | @ Hotchkiss School | Oct 11 | 3:15 PM | Hotchkiss School | 3 - 1 | Away | |
| Varsity B Volleyball | vs. Forman School | Oct 11 | 3:15 PM | Home | 0 - 3 | Home | |
| Varsity Field Hockey | @ Hotchkiss School | Oct 11 | 3:15 PM | Hotchkiss School | 2 - 0 | Away | |
| Blue Dog Bikes - Racing Team | @ South Kent School | Oct 11 | 3:30 PM | South Kent School | - | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Oct 11 | 3:30 PM | Indian Mountain School | 5 - 4 | Away | |
| Varsity Cross Country | @ Millbrook School | Oct 11 | 3:30 PM | Millbrook School | - | Away | |
| Varsity B Soccer | @ Washington Montessori School (WMS) | Oct 12 | 3:45 PM | Washington Montessori School (WMS) | 3 - 0 | Away | |
| Girl's Varsity Soccer | vs. Washington Montessori School (WMS) | Oct 12 | 3:45 PM | Home | 8 - 3 | Home | |
| Varsity Cross Country | vs. Indian Mountain School | Oct 13 | 3:15 PM | Home | 25 - 31 | Home | |
| Varsity Football | vs. Avon Old Farms School | Oct 13 | 4:00 PM | Home | 28 - 14 | Home | |
| Varsity Cross Country | vs. TBD | Oct 14 | 2:30 PM | Home | - | Home | Rescheduled to Oct 13 |
| Girl's Varsity Soccer | vs. Choate Rosemary Hall | Oct 14 | 2:30 PM | Home | 9 - 0 | Home | |
| Boy's Varsity Soccer | vs. Indian Mountain School | Oct 14 | 2:30 PM | Home | 0 - 4 | Home | |
| Varsity Volleyball | vs. Taft School | Oct 14 | 2:30 PM | Home | 3 - 0 | Home | |
| Varsity Field Hockey | vs. Canterbury School | Oct 14 | 2:30 PM | Home | 4 - 0 | Home | |
| Varsity B Soccer | vs. Trinity Pawling School | Oct 17 | 3:45 PM | Home | 2 - 2 | Home | |
| Girl's Varsity Soccer | @ Kingswood-Oxford School | Oct 18 | 3:00 PM | Kingswood-Oxford School | 0 - 7 | Away | |
| Varsity Football | @ Kingswood-Oxford School | Oct 18 | 3:00 PM | Kingswood-Oxford School | 16 - 8 | Away | |
| Varsity B Soccer | @ Indian Mountain School | Oct 18 | 3:15 PM | Indian Mountain School | 0 - 8 | Away | |
| Varsity B Volleyball | vs. Hopkins School | Oct 18 | 3:15 PM | Home | 0 - 3 | Home | |
| Blue Dog Bikes - Racing Team | @ Trinity Pawling School | Oct 18 | 3:30 PM | Trinity Pawling School | - | Away | |
| Junior Blue Soccer | vs. Mizzentop | Oct 18 | 4:10 PM | Home | 7 - 4 | Home | |
| Varsity B Field Hockey | vs. Mizzentop | Oct 18 | 4:10 PM | Home | 4 - 0 | Home | |
| Junior Blue Soccer | vs. Renbrook School | Oct 19 | 4:00 PM | Home | 7 - 1 | Home | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 20 | 3:30 PM | Home | 1 - 2 | Away | |
| Junior Red Soccer | vs. Washington Montessori School (WMS) | Oct 23 | 3:30 PM | Home | 1 - 4 | Home | |
| Varsity Field Hockey | vs. Renbrook School | Oct 24 | 3:45 PM | Home | 2 - 0 | Home | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 24 | 4:00 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Soccer | @ Trinity Pawling School | Oct 24 | 4:00 PM | Trinity Pawling School | 2 - 6 | Away | |
| Varsity Field Hockey | @ Frederick Gunn School | Oct 25 | 2:00 PM | Home | 2 - 0 | Away | |
| Varsity Volleyball | vs. Westover School | Oct 25 | 3:15 PM | Home | 3 - 0 | Home | |
| Varsity B Volleyball | vs. Hotchkiss School | Oct 25 | 3:15 PM | Home | 1 - 2 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Oct 25 | 3:30 PM | Home | 7 - 5 | Home | |
| Girl's Varsity Soccer | @ Berkshire School | Oct 25 | 3:30 PM | Berkshire School | 0 - 3 | Away | |
| Boy's Varsity Soccer | @ Choate Rosemary Hall | Oct 25 | 3:30 PM | Choate Rosemary Hall | 2 - 1 | Away | |
| Blue Dog Bikes - Racing Team | @ Berkshire School | Oct 25 | 3:30 PM | Berkshire School | - | Away | |
| Varsity Cross Country | @ Indian Mountain School | Oct 25 | 4:00 PM | Indian Mountain School | - | Away | |
| Varsity B Soccer | vs. Maplebrook School | Oct 26 | 3:30 PM | Home | 7 - 1 | Home | |
| Varsity B Field Hockey | vs. Mizzentop | Oct 26 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity Soccer | vs. Indian Mountain School | Oct 27 | 3:15 PM | Home | 2 - 8 | Home | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 27 | 3:15 PM | Indian Mountain School | 3 - 2 | Away | |
| Varsity Volleyball | vs. Indian Mountain School | Oct 27 | 3:15 PM | Home | 3 - 0 | Home | |
| Varsity Cross Country | @ Dutchess Day School | Oct 27 | 3:30 PM | Dutchess Day School | - | Away | |
| Varsity Field Hockey | @ Taft School | Oct 27 | 4:00 PM | Taft School | 3 - 0 | Away | |
| Varsity Football | vs. Eaglebrook School | Oct 28 | 2:00 PM | Home | 6 - 8 | Home | |
| Varsity Field Hockey | vs. Loomis Chaffee | Oct 28 | 2:30 PM | Home | - | Home | Cancelled |
| Junior Red Soccer | vs. Washington Montessori School (WMS) | Oct 30 | 3:30 PM | Home | 1 - 4 | Home | |
| Blue Dog Bikes - Racing Team | @ Mountain Biking Championships | Nov 1 | 3:00 PM | Norbrook Farm | - | Away | |
| Varsity Field Hockey | @ Westminster School | Nov 1 | 3:15 PM | Westminster School | 5 - 0 | Away | |
| Boy's Varsity Soccer | vs. Westminster School | Nov 1 | 3:15 PM | Home | 3 - 3 | Home | |
| Varsity Volleyball | vs. Choate Rosemary Hall | Nov 1 | 3:15 PM | Home | 3 - 1 | Home | |
| Varsity Cross Country | @ Kingswood-Oxford School | Nov 1 | 3:30 PM | Kingswood-Oxford School | - | Away | |
| Girl's Varsity Soccer | @ Foote School | Nov 1 | 3:30 PM | Foote School | - | Away | Cancelled |
| Varsity Football | vs. Brunswick School | Nov 1 | 3:45 PM | Home | 21 - 8 | Home | |
| Varsity B Field Hockey | @ Mizzentop | Nov 2 | 3:45 PM | Mizzentop | 6 - 0 | Away | |
| Girl's Varsity Soccer | @ Ethel Walker School | Nov 2 | 3:45 PM | Ethel Walker School | 0 - 4 | Away | |
| Junior Blue Soccer | @ Dutchess Day School | Nov 2 | 3:45 PM | Dutchess Day School | 7 - 2 | Away | |
| Varsity B Soccer | vs. Dutchess Day School | Nov 2 | 3:45 PM | Home | 0 - 1 | Home | |
| Boy's Varsity Soccer | @ Avon Old Farms School | Nov 2 | 4:00 PM | Avon Old Farms School | 0 - 2 | Away | |
| Varsity Volleyball | @ Taft School | Nov 2 | 4:00 PM | Taft School | 3 - 0 | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Nov 3 | 3:30 PM | Home | - | Home | |
| Varsity B Field Hockey | @ Dutchess Day School | Nov 3 | 3:30 PM | Dutchess Day School | 0 - 2 | Away | |
| Varsity B Soccer | @ Sherman Middle School | Nov 3 | 3:30 PM | Sherman Middle School | 1 - 4 | Away | |
| Varsity B Volleyball | @ Hopkins School | Nov 3 | 4:15 PM | Hopkins School | 2 - 1 | Away | |
| Varsity Field Hockey | @ Frederick Gunn School | Nov 3 | 4:15 PM | Frederick Gunn School | - | Away | Cancelled |
| Boy's Varsity Soccer | @ Eaglebrook Boys Soccer Tournament | Nov 4 | 7:30 AM | Eaglebrook School | - | Away | |
| Girl's Varsity Soccer | @ IMS Girls Soccer Tournament | Nov 4 | 10:30 AM | Indian Mountain School | - | Away | |
| Varsity Volleyball | vs. Rick Spooner Volleyball Classic | Nov 4 | 2:00 PM | Home | - | Home | |
| Varsity B Field Hockey | @ Renbrook School | Nov 7 | 3:15 PM | Renbrook School | 0 - 1 | Away | |
| Varsity Football | vs. Hopkins School | Nov 8 | 3:00 PM | Home | 30 - 8 | Home | |
| Girl's Varsity Soccer | vs. Westminster School | Nov 8 | 3:00 PM | Home | 6 - 1 | Home | |
| Varsity Field Hockey | vs. Hotchkiss School | Nov 8 | 3:00 PM | Hotchkiss School | 4 - 0 | Home | |
| Boy's Varsity Soccer | @ Salisbury School | Nov 8 | 3:15 PM | Salisbury School | 4 - 7 | Away | |
| Varsity B Volleyball | @ Forman School | Nov 8 | 3:15 PM | Forman School | - | Away | Cancelled |
| Varsity Volleyball | vs. Kingswood-Oxford School | Nov 8 | 3:30 PM | Home | 3 - 0 | Home | |
| Varsity Cross Country | @ Washington Montessori School (WMS) | Nov 8 | 3:30 PM | Washington Montessori School (WMS) | - | Away | |
| Girl's Varsity Soccer | @ Indian Mountain School | Nov 9 | 6:30 PM | Hotchkiss School | 0 - 6 | Away | |
| Varsity B Soccer | vs. Indian Mountain School | Nov 10 | 2:45 PM | Home | 0 - 6 | Home | |
| Junior Blue Soccer | @ Indian Mountain School | Nov 10 | 2:45 PM | Indian Mountain School | 5 - 4 | Away | |
| Varsity Cross Country | vs. Indian Mountain School | Nov 10 | 2:45 PM | Home | 40 - 21 | Home | |
| Boy's Varsity Soccer | @ Indian Mountain School | Nov 10 | 2:45 PM | Indian Mountain School | 0 - 6 | Away | |
| Varsity Volleyball | @ Indian Mountain School | Nov 10 | 3:15 PM | Indian Mountain School | 3 - 1 | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Nov 10 | 3:15 PM | Home | 1 - 2 | Home | |
| Boy's Varsity Ice Hockey | @ Rectory School | Dec 2 | 12:30 PM | Rectory School | 2 - 2 | Away | |
| Girl's Varsity Ice Hockey | vs. Choate Rosemary Hall | Dec 6 | 3:00 PM | Home | 8 - 1 | Home | |
| Boy's Varsity Ice Hockey | @ Westminster School | Dec 6 | 5:30 PM | Westminster School | 10 - 0 | Away | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Dec 7 | 3:30 PM | Home | 7 - 11 | Home | |
| Girl's Varsity Basketball | vs. Sherman Middle School | Dec 7 | 3:30 PM | Home | 24 - 9 | Home | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Dec 7 | 7:15 PM | Home | 4 - 2 | Home | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Dec 8 | 2:15 PM | Home | 3 - 7 | Home | |
| Boy's Varsity B Basketball | vs. Berkshire Waldorf School | Dec 8 | 3:45 PM | Home | 53 - 15 | Home | |
| Boy's Varsity Basketball | @ Avon Old Farms School | Dec 8 | 4:00 PM | Avon Old Farms School | 57 - 34 | Away | |
| Girl's Varsity Ice Hockey | vs. Frederick Gunn School | Jan 5 | 4:00 PM | Home | 10 - 1 | Home | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 5 | 5:30 PM | Home | 5 - 3 | Home | |
| Boy's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 6 | 6:00 AM | Upland Country Day School | - | Away | |
| Boy's Varsity Ice Hockey | @ NCCS (New Canaan Country School) | Jan 6 | 12:00 PM | Upland Country Day School | 6 - 1 | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 6 | 4:15 PM | Upland Country Day School | 2 - 4 | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 7 | 8:00 AM | Upland Country Day School | - | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 7 | 10:30 AM | Upland Country Day School | 4 - 1 | Away | |
| Boy's Varsity Ice Hockey | @ NCCS (New Canaan Country School) | Jan 7 | 1:00 PM | Upland Country Day School | 7 - 2 | Away | |
| Boy's Varsity B Basketball | @ Dutchess Day School | Jan 9 | 3:45 PM | Home | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Avon Old Farms School | Jan 9 | 4:50 PM | Avon Old Farms School | - | Away | Cancelled |
| Girl's Varsity Ice Hockey | vs. Kent School | Jan 10 | 3:15 PM | Home | 8 - 2 | Home | |
| Boy's Varsity Basketball | @ Frederick Gunn School | Jan 10 | 3:15 PM | Frederick Gunn School | 57 - 46 | Away | |
| Girl's Varsity Basketball | vs. Kingswood-Oxford School | Jan 10 | 3:30 PM | Home | 15 - 8 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 10 | 4:30 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity B Basketball | vs. Sherman Middle School | Jan 11 | 3:30 PM | Home | 33 - 40 | Home | |
| Boy's Varsity Basketball | @ Brunswick School | Jan 11 | 4:00 PM | Brunswick School | 67 - 50 | Away | |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Jan 12 | 3:30 PM | Home | 34 - 14 | Home | |
| Girl's Varsity B Basketball | vs. Indian Mountain School | Jan 12 | 3:30 PM | Home | 19 - 7 | Home | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Jan 12 | 4:00 PM | Home | 5 - 1 | Home | |
| Varsity B Ice Hockey | @ Eaglebrook School | Jan 12 | 4:00 PM | Eaglebrook School | 4 - 1 | Away | |
| Girl's Varsity Ice Hockey | @ Choate Rosemary Hall | Jan 12 | 4:15 PM | Choate Rosemary Hall | 4 - 4 | Away | |
| Girl's Varsity Basketball | @ Choate Rosemary Hall | Jan 13 | 3:00 PM | Choate Rosemary Hall | 26 - 32 | Away | |
| Girl's Varsity B Basketball | @ Renbrook School | Jan 16 | 3:45 PM | Renbrook School | - | Away | Cancelled |
| Boy's Varsity B Basketball | @ Trinity Pawling School | Jan 16 | 4:00 PM | Trinity Pawling School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | vs. Kent School | Jan 17 | 2:30 PM | Home | 10 - 2 | Home | |
| Girl's Varsity Basketball | @ Indian Mountain School | Jan 17 | 2:45 PM | Indian Mountain School | 27 - 22 | Away | |
| Boy's Varsity Basketball | @ Canterbury School | Jan 17 | 3:00 PM | Canterbury School | 57 - 39 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 17 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity B Basketball | vs. Maplebrook School | Jan 17 | 3:30 PM | Home | 44 - 23 | Home | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Jan 17 | 4:15 PM | Home | 10 - 0 | Home | |
| Boy's Varsity Ice Hockey | vs. Fairfield Country Day | Jan 18 | 3:00 PM | Home | 1 - 2 | Home | |
| Boy's Varsity Basketball | vs. Oakwood Friends School | Jan 18 | 3:30 PM | Home | 60 - 25 | Home | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Jan 18 | 3:30 PM | Washington Montessori School (WMS) | 34 - 8 | Away | |
| Girl's Varsity B Basketball | @ Berkshire Waldorf School | Jan 18 | 3:45 PM | Home | 6 - 4 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Jan 18 | 3:45 PM | Home | 2 - 1 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Jan 19 | 3:30 PM | Catamount Ski Area | - | Away | Cancelled |
| Girl's Varsity Basketball | vs. Frederick Gunn School | Jan 19 | 4:00 PM | Home | 22 - 13 | Home | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 19 | 4:30 PM | Home | 0 - 1 | Home | |
| Girl's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 20 | 6:00 AM | Upland Country Day School | - | Away | |
| Girl's Varsity Ice Hockey | @ Washington Pride | Jan 20 | 12:00 PM | Upland Country Day School | 1 - 2 | Away | |
| Girl's Varsity Ice Hockey | @ Upland Country Day School | Jan 20 | 4:15 PM | Upland Country Day School | 1 - 6 | Away | |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 20 | 4:30 PM | Cardigan Mountain School | 2 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 21 | 9:00 AM | Cardigan Mountain School | 6 - 4 | Away | |
| Girl's Varsity Ice Hockey | @ Ed Snider (Travel Hockey) | Jan 21 | 9:30 AM | Upland Country Day School | 6 - 1 | Away | |
| Girl's Varsity Ice Hockey | @ Ed Snider (Travel Hockey) | Jan 21 | 12:00 PM | Upland Country Day School | 4 - 2 | Away | |
| Boy's Varsity B Basketball | @ Sherman Middle School | Jan 23 | 3:45 PM | Sherman Middle School | 41 - 39 | Away | |
| Boy's Varsity Ice Hockey | @ Berkshire School | Jan 24 | 2:30 PM | Berkshire School | 7 - 4 | Away | |
| Girl's Varsity Ice Hockey | @ Canterbury School | Jan 24 | 3:00 PM | Canterbury School | 6 - 2 | Away | |
| Girl's Varsity Basketball | @ Canterbury School | Jan 24 | 3:00 PM | Canterbury School | 36 - 16 | Away | |
| Boy's Varsity B Basketball | vs. Oakwood Friends School | Jan 24 | 3:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity Basketball | vs. Avon Old Farms School | Jan 24 | 3:30 PM | Home | 68 - 34 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Jan 24 | 3:30 PM | Home | 12 - 0 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 24 | 4:30 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity B Basketball | vs. Washington Montessori School (WMS) | Jan 25 | 3:30 PM | Home | 22 - 20 | Home | |
| Winter Volleyball | @ Dutchess Day School | Jan 25 | 3:45 PM | Dutchess Day School | 3 - 0 | Away | |
| Boy's Jr. Blue Basketball | vs. Renbrook School | Jan 25 | 3:45 PM | Home | 19 - 42 | Home | |
| Boy's Varsity Basketball | @ Indian Mountain School | Jan 26 | 3:00 PM | Indian Mountain School | 79 - 44 | Away | |
| Varsity Ski Team | @ Indian Mountain School | Jan 26 | 3:30 PM | Catamount Ski Area | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Jan 26 | 6:30 PM | Silo Ridge | 4 - 0 | Away | |
| Girl's Varsity Ice Hockey | @ Kent School | Jan 27 | 2:30 PM | Kent School | 1 - 4 | Away | |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Jan 29 | 3:30 PM | Home | 22 - 10 | Home | |
| Boy's Varsity Ice Hockey | vs. Brunswick School | Jan 29 | 3:45 PM | Home | 7 - 5 | Home | |
| Boy's Varsity B Basketball | @ Mizzentop | Jan 29 | 4:00 PM | Mizzentop / Patterson Recreation Center | 38 - 18 | Away | |
| Boy's Varsity Basketball | vs. Trinity Pawling School | Jan 29 | 4:00 PM | Home | 90 - 71 | Home | |
| Girl's Varsity B Basketball | @ Sherman Middle School | Jan 30 | 3:45 PM | Sherman Middle School | 10 - 27 | Away | |
| Boy's Varsity Ice Hockey | vs. Taft School | Jan 31 | 2:30 PM | Home | - | Home | |
| Varsity B Ice Hockey | vs. Taft School | Jan 31 | 2:30 PM | Home | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | @ Millbrook School | Jan 31 | 3:00 PM | Millbrook School | 3 - 2 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 31 | 3:00 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Hotchkiss School | Jan 31 | 3:15 PM | Home | 28 - 13 | Home | |
| Boy's Varsity B Basketball | vs. Hopkins School | Jan 31 | 3:30 PM | Home | 30 - 55 | Home | |
| Boy's Varsity Basketball | @ Taft School | Jan 31 | 4:00 PM | Taft School | 80 - 45 | Away | |
| Winter Volleyball | @ Dutchess Day School | Feb 1 | 3:45 PM | Dutchess Day School | 3 - 0 | Away | |
| Girl's Varsity B Basketball | vs. Renbrook School | Feb 1 | 3:45 PM | Home | 12 - 8 | Home | |
| Girl's Varsity Ice Hockey | @ Taft School | Feb 1 | 4:00 PM | Taft School | 8 - 1 | Away | |
| Varsity B Ice Hockey | @ Indian Mountain School | Feb 2 | 3:00 PM | Hotchkiss School | 6 - 2 | Away | |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Feb 2 | 3:00 PM | Hotchkiss School | 6 - 1 | Away | |
| Boy's Varsity B Basketball | vs. Indian Mountain School | Feb 2 | 3:15 PM | Home | 53 - 19 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 7 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Feb 7 | 3:30 PM | Home | 31 - 10 | Home | |
| Girl's Varsity Ice Hockey | vs. Hotchkiss School | Feb 7 | 3:30 PM | Home | 7 - 0 | Home | |
| Girl's Varsity B Basketball | vs. Berkshire Waldorf School | Feb 7 | 3:45 PM | Home | - | Home | Cancelled |
| Boy's Varsity B Basketball | @ Berkshire Waldorf School | Feb 7 | 3:45 PM | Home | - | Away | Cancelled |
| Girl's Varsity Basketball | vs. Oakwood Friends School | Feb 8 | 3:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 8 | 3:30 PM | Washington Montessori School (WMS) | 56 - 28 | Away | |
| Boy's Varsity Ice Hockey | @ Fairfield Country Day | Feb 8 | 3:30 PM | Fairfield Country Day School | 1 - 0 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Feb 8 | 3:45 PM | Home | 3 - 0 | Home | |
| Boy's Jr. Blue Basketball | @ Mizzentop | Feb 8 | 4:00 PM | Mizzentop | 8 - 32 | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 9 | 2:30 PM | Lufkin Rink - Rink - 2600 | 6 - 0 | Home | |
| Boy's Varsity Basketball | vs. Salisbury School | Feb 9 | 3:00 PM | Home | 70 - 51 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Feb 9 | 3:30 PM | Catamount Ski Area | - | Away | Cancelled |
| Girl's Varsity B Basketball | @ Hotchkiss School | Feb 9 | 4:00 PM | Hotchkiss School | 3 - 20 | Away | |
| Girl's Varsity Ice Hockey | vs. Berkshire School | Feb 9 | 4:45 PM | Home | 7 - 1 | Home | |
| Boy's Varsity B Basketball | @ TBD | Feb 10 | 9:00 AM | Maplebrook School | 2nd | Away | |
| Boy's Varsity Basketball | vs. Indian Mountain School | Feb 10 | 1:00 PM | Home | 84 - 48 | Home | |
| Girl's Varsity Basketball | vs. Canterbury School | Feb 10 | 1:30 PM | Home | 36 - 29 | Home | |
| Girl's Varsity Ice Hockey | @ Westminster School | Feb 10 | 1:30 PM | Westminster School | 7 - 3 | Away | |
| Boy's Varsity Ice Hockey | vs. Kent School | Feb 10 | 2:30 PM | Home | 7 - 0 | Home | |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Feb 12 | 3:30 PM | Home | 28 - 16 | Home | |
| Boy's Varsity B Basketball | vs. Trinity Pawling School | Feb 13 | 4:00 PM | Home | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | vs. Brunswick School | Feb 13 | 4:00 PM | Home | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | vs. Canterbury School | Feb 14 | 2:30 PM | Home | 5 - 0 | Home | |
| Girl's Varsity B Basketball | vs. Ethel Walker School | Feb 14 | 3:00 PM | Home | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 14 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Indian Mountain School | Feb 14 | 3:15 PM | Home | 39 - 26 | Home | |
| Boy's Varsity B Basketball | @ Berkshire Waldorf School | Feb 14 | 3:45 PM | Berkshire Waldorf School - Bard College @ Simon's Rock | - | Away | Cancelled |
| Boy's Varsity Basketball | @ Hopkins School | Feb 14 | 4:15 PM | Hopkins School | 45 - 29 | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 14 | 4:15 PM | Home | 5 - 0 | Home | |
| Boy's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 15 | 3:30 PM | Home | 53 - 29 | Home | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 15 | 3:30 PM | Washington Montessori School (WMS) | 22 - 15 | Away | |
| Winter Volleyball | @ Dutchess Day School | Feb 15 | 3:45 PM | Dutchess Day School | 1 - 2 | Away | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Feb 16 | 3:00 PM | Indian Mountain School | 32 - 22 | Away | |
| Varsity Ski Team | @ Indian Mountain School | Feb 16 | 3:30 PM | Catamount Ski Area | - | Away | |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 16 | 3:30 PM | Home | 4 - 1 | Home | |
| Boy's Varsity Basketball | @ Frederick Gunn School | Feb 16 | 4:00 PM | Frederick Gunn School | 56 - 36 | Away | |
| Girl's Varsity Basketball | @ Frederick Gunn School | Feb 16 | 4:15 PM | Frederick Gunn School | 27 - 13 | Away | |
| Girl's Varsity Ice Hockey | vs. TBD | Feb 17 | 8:00 AM | Home | - | Home | |
| Girl's Varsity Ice Hockey | vs. Danbury Hat Tricks U14 Girls | Feb 17 | 10:00 AM | Lufkin Rink - Rink - 2600 | 6 - 2 | Home | |
| Girl's Varsity Ice Hockey | vs. Shoreline Sharks | Feb 17 | 1:00 PM | Lufkin Rink - Rink - 2600 | 3 - 3 | Home | |
| Boy's Varsity Basketball | vs. Westminster School | Feb 17 | 2:30 PM | Home | 72 - 40 | Home | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Feb 17 | 3:30 PM | Lufkin Rink - Rink - 2600 | 3 - 1 | Home | |
| Boy's Varsity Basketball | vs. Canterbury School | Feb 19 | 4:30 PM | Home | 63 - 48 | Home | |
| Girl's Varsity Basketball | vs. Berkshire School | Feb 19 | 4:45 PM | Home | 32 - 16 | Home | |
| Girl's Varsity B Basketball | vs. Ethel Walker School | Feb 20 | 4:00 PM | Home | 8 - 31 | Home | |
| Varsity B Ice Hockey | @ Eaglebrook School | Feb 20 | 4:30 PM | Home | 1 - 2 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 21 | 11:00 AM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Ice Hockey | vs. Frederick Gunn School | Feb 21 | 2:30 PM | Home | 7 - 1 | Home | |
| Boy's Varsity Ice Hockey | @ Salisbury School | Feb 21 | 3:00 PM | Salisbury School | 2 - 3 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 21 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity B Basketball | @ Indian Mountain School | Feb 21 | 3:45 PM | Home | 48 - 38 | Away | |
| Boy's Varsity Basketball | @ Berkshire School | Feb 21 | 4:00 PM | Berkshire School | 61 - 50 | Away | |
| Boy's Jr. Blue Basketball | vs. Dutchess Day School | Feb 21 | 4:00 PM | Home | 32 - 15 | Home | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Feb 21 | 4:15 PM | Home | 10 - 1 | Home | |
| Boy's Jr. Blue Basketball | @ Renbrook School | Feb 22 | 3:45 PM | Renbrook School | 32 - 32 | Away | |
| Boy's Varsity Basketball | vs. Renbrook School | Feb 22 | 3:45 PM | Athletics Building - Blue Dog Gym - BD Gym | 64 - 33 | Home | |
| Winter Volleyball | vs. Dutchess Day School | Feb 22 | 3:45 PM | Home | 2 - 1 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 23 | 2:30 PM | Home | 6 - 0 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Feb 23 | 3:30 PM | Catamount Ski Area | - | Away | |
| Girl's Varsity B Basketball | @ Indian Mountain School | Feb 23 | 3:30 PM | Home | 16 - 9 | Away | |
| Girl's Varsity Basketball | vs. TBD | Feb 23 | 4:30 PM | Home | - | Home | Rescheduled to Feb 19 |
| Girl's Varsity Ice Hockey | vs. Berkshire School | Feb 23 | 4:30 PM | Home | 7 - 3 | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 24 | 8:00 AM | Home | - | Home | |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 24 | 2:00 PM | Home | 10 - 0 | Home | |
| Boy's Varsity B Basketball | @ Taft School | Feb 24 | 2:30 PM | Taft School | - | Away | Cancelled |
| Girl's Varsity Basketball | vs. Ethel Walker School | Feb 24 | 3:00 PM | Home | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Feb 24 | 5:00 PM | Home | 4 - 2 | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 25 | 8:00 AM | Home | - | Home | |
| Boy's Varsity Basketball | @ TBD | Feb 25 | 9:00 AM | Suffield Academy | - | Away | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Feb 25 | 9:30 AM | Home | 1 - 3 | Home | |
| Boy's Varsity Ice Hockey | vs. Cardigan Mountain School | Feb 25 | 2:00 PM | Home | 2 - 5 | Home | |
| Boy's Varsity B Lacrosse | @ Hamden Hall | Apr 9 | 4:00 PM | Hamden Hall | 1 - 12 | Away | |
| Varsity A Tennis | @ Millbrook School | Apr 9 | 4:15 PM | Millbrook School | 6 - 3 | Away | |
| Varsity Softball | @ Westminster School | Apr 10 | 3:15 PM | Westminster School | 12 - 14 | Away | |
| Varsity Baseball | vs. Berkshire School | Apr 10 | 3:15 PM | Home | 3 - 8 | Home | |
| Varsity B Tennis | @ Mizzentop | Apr 10 | 4:00 PM | Quaker Hill Country Club | 6 - 0 | Away | |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | Apr 12 | 3:00 PM | Indian Mountain School | 11 - 5 | Away | |
| Varsity B Tennis | @ Indian Mountain School | Apr 12 | 3:00 PM | Indian Mountain School | - | Away | Cancelled |
| Varsity Baseball | vs. Oakwood Friends School | Apr 12 | 4:00 PM | Home | - | Home | Cancelled |
| Girl's Varsity Lacrosse | vs. Kent School | Apr 12 | 4:15 PM | Home | 6 - 7 | Home | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | Apr 12 | 4:15 PM | Indian Mountain School | 1 - 8 | Away | |
| Boy's Varsity Lacrosse | @ Hamden Hall | Apr 12 | 4:30 PM | Hamden Hall | 9 - 6 | Away | |
| Boy's Varsity Lacrosse | vs. Westminster School | Apr 13 | 2:30 PM | Home | - | Home | Cancelled |
| Varsity Softball | vs. Choate Rosemary Hall | Apr 13 | 2:30 PM | Home | - | Home | Cancelled |
| Varsity B Tennis | vs. Renbrook School | Apr 16 | 3:45 PM | Home | 8 - 0 | Home | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | Apr 16 | 4:00 PM | Home | - | Home | Cancelled |
| Varsity Softball | @ Hamden Hall | Apr 16 | 4:00 PM | Hamden Hall | 15 - 11 | Away | |
| Boy's Varsity B Lacrosse | @ Trinity Pawling School | Apr 16 | 4:00 PM | Trinity Pawling School | 2 - 6 | Away | |
| Varsity A Tennis | vs. Taft School | Apr 17 | 3:00 PM | Home | 5 - 4 | Home | |
| Varsity Baseball | @ Berkshire School | Apr 17 | 3:15 PM | Berkshire School | 15 - 3 | Away | |
| Girl's Varsity Lacrosse | vs. Berkshire School | Apr 17 | 3:15 PM | Home | 12 - 5 | Home | |
| Girl's Varsity B Lacrosse | @ Dutchess Day School | Apr 17 | 3:30 PM | Dutchess Day School | 2 - 10 | Away | |
| Boy's Varsity B Lacrosse | vs. Dutchess Day School | Apr 17 | 3:45 PM | Home | 1 - 9 | Home | |
| Boy's Varsity Lacrosse | @ Rectory School | Apr 17 | 4:00 PM | Avon Old Farms School | 13 - 6 | Away | |
| Varsity Softball | @ Renbrook School | Apr 18 | 3:30 PM | Renbrook School | - | Away | Cancelled |
| Varsity B Tennis | vs. Indian Mountain School | Apr 19 | 3:15 PM | Home | 7 - 2 | Home | |
| Varsity Baseball | vs. Trinity Pawling School | Apr 19 | 4:00 PM | Home | 7 - 6 | Home | |
| Boy's Varsity Lacrosse | @ Taft School | Apr 19 | 4:00 PM | Taft School | 6 - 4 | Away | |
| Girl's Varsity Lacrosse | @ Hotchkiss School | Apr 19 | 4:30 PM | Hotchkiss School | 3 - 14 | Away | |
| Varsity A Tennis | @ Hotchkiss School | Apr 19 | 4:30 PM | Hotchkiss School | 0 - 7 | Away | |
| Varsity Baseball | @ Canterbury School | Apr 22 | 4:00 PM | Canterbury School | 1 - 11 | Away | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | Apr 23 | 4:00 PM | Indian Mountain School | 2 - 9 | Away | |
| Varsity B Tennis | @ Dutchess Day School | Apr 23 | 4:00 PM | Dutchess Day School | 4 - 2 | Away | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | Apr 23 | 4:15 PM | Home | 8 - 3 | Home | |
| Varsity Crew | @ Salisbury School | Apr 24 | 3:00 PM | Salisbury School | - | Away | |
| Varsity A Tennis | vs. Hotchkiss School | Apr 24 | 3:00 PM | Home | 0 - 8 | Home | |
| Varsity Softball | vs. Indian Mountain School | Apr 24 | 3:15 PM | Home | 12 - 7 | Home | |
| Girl's Varsity Lacrosse | vs. Indian Mountain School | Apr 24 | 3:15 PM | Home | 6 - 12 | Home | |
| Boy's Varsity B Lacrosse | @ Dutchess Day School | Apr 24 | 3:30 PM | Home | 2 - 8 | Away | |
| Boy's Varsity Lacrosse | vs. Hopkins School | Apr 24 | 3:30 PM | Home | 12 - 1 | Home | |
| Varsity B Baseball | vs. Berkshire Waldorf School | Apr 24 | 4:00 PM | Home | 5 - 10 | Home | |
| Varsity Baseball | @ Indian Mountain School | Apr 26 | 3:15 PM | Indian Mountain School | - | Away | Cancelled |
| Varsity B Tennis | vs. Indian Mountain School | Apr 26 | 3:15 PM | Home | 5 - 6 | Home | |
| Varsity Baseball | @ Suffield Academy | Apr 26 | 4:00 PM | Home | 10 - 5 | Away | |
| Varsity A Tennis | @ Berkshire School | Apr 26 | 4:00 PM | Berkshire School | 2 - 7 | Away | |
| Girl's Varsity B Lacrosse | vs. Berkshire Waldorf School | Apr 26 | 4:00 PM | Home | - | Home | Cancelled |
| Boy's Varsity Lacrosse | vs. Hamden Hall | Apr 26 | 4:00 PM | Home | - | Home | |
| Girl's Varsity Lacrosse | @ Loomis Chaffee | Apr 26 | 4:15 PM | Loomis Chaffee | 6 - 7 | Away | |
| Varsity Baseball | vs. Oakwood Friends School | Apr 29 | 4:00 PM | Home | 12 - 2 | Home | |
| Varsity B Baseball | @ Indian Mountain School | Apr 30 | 3:45 PM | Indian Mountain School | - | Away | Cancelled |
| Varsity A Tennis | vs. Indian Mountain School | Apr 30 | 4:00 PM | Home | 4 - 5 | Home | |
| Varsity B Tennis | @ Hamden Hall | Apr 30 | 4:00 PM | Hamden Hall | 7 - 3 | Away | |
| Boy's Varsity B Lacrosse | vs. Hamden Hall | Apr 30 | 4:00 PM | Home | 0 - 11 | Home | |
| Boy's Varsity Lacrosse | @ Avon Old Farms School | May 1 | 3:15 PM | Avon Old Farms School | 1 - 6 | Away | |
| Girl's Varsity Lacrosse | @ Millbrook School | May 1 | 3:30 PM | Millbrook School | 15 - 10 | Away | |
| Varsity Crew | @ Hotchkiss School | May 1 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity Baseball | @ Brunswick School | May 1 | 3:30 PM | Brunswick School | 2 - 12 | Away | |
| Varsity Softball | vs. Sherman Middle School | May 1 | 3:45 PM | Home | 15 - 7 | Home | |
| Varsity B Tennis | @ Washington Montessori School (WMS) | May 2 | 3:45 PM | Washington Montessori School (WMS) | 8 - 1 | Away | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | May 3 | 3:15 PM | Home | 9 - 5 | Home | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | May 3 | 3:15 PM | Home | 2 - 8 | Home | |
| Varsity Crew | @ Choate Rosemary Hall | May 3 | 3:30 PM | Choate Rosemary Hall | - | Away | |
| Varsity B Baseball | vs. Kent Center School | May 3 | 3:45 PM | Home | 1 - 17 | Home | |
| Varsity Baseball | vs. Canterbury School | May 4 | 2:30 PM | Home | 9 - 4 | Home | |
| Varsity Softball | vs. Westminster School | May 4 | 2:30 PM | Home | 19 - 6 | Home | |
| Varsity A Tennis | vs. Trinity Pawling School | May 4 | 2:30 PM | Home | 7 - 0 | Home | |
| Boy's Varsity Lacrosse | vs. Indian Mountain School | May 4 | 2:30 PM | Home | 7 - 8 | Home | |
| Girl's Varsity Lacrosse | vs. Westminster School | May 4 | 2:30 PM | Home | - | Home | Cancelled |
| Varsity Crew | @ Founder's Day Regatta | May 5 | 7:30 AM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity Softball | @ Foote School | May 7 | 4:00 PM | Foote School | 15 - 9 | Away | |
| Varsity B Tennis | vs. Westminster School | May 8 | 2:45 PM | Home | 5 - 1 | Home | |
| Girl's Varsity Lacrosse | vs. Frederick Gunn School | May 8 | 2:45 PM | Home | 11 - 1 | Home | |
| Boy's Varsity Lacrosse | vs. Avon Old Farms School | May 8 | 3:00 PM | Home | 8 - 9 | Home | |
| Varsity B Baseball | vs. Indian Mountain School | May 8 | 3:15 PM | Home | 4 - 15 | Home | |
| Varsity Baseball | vs. Salisbury School | May 8 | 3:30 PM | Home | 9 - 10 | Home | |
| Varsity Crew | @ Berkshire School | May 8 | 3:30 PM | Camp Sloane | - | Away | |
| Varsity Softball | @ Sherman Middle School | May 9 | 3:45 PM | Sherman Middle School | 8 - 14 | Away | |
| Boy's Varsity B Lacrosse | @ Renbrook School | May 9 | 3:45 PM | Renbrook School | 2 - 9 | Away | |
| Varsity B Tennis | @ Indian Mountain School | May 10 | 3:15 PM | Indian Mountain School | - | Away | Cancelled |
| Varsity Crew | @ Canterbury School | May 10 | 3:30 PM | GMS Rowing Center | - | Away | Cancelled |
| Varsity B Baseball | @ Kent Center School | May 10 | 3:30 PM | Kent Center School | 0 - 12 | Away | |
| Varsity Baseball | vs. Frederick Gunn School | May 10 | 3:45 PM | Home | 12 - 1 | Home | |
| Varsity A Tennis | vs. Frederick Gunn School | May 10 | 3:45 PM | Home | 6 - 1 | Home | |
| Girl's Varsity B Lacrosse | vs. Berkshire Waldorf School | May 10 | 4:00 PM | Home | 6 - 2 | Home | |
| Boy's Varsity Lacrosse | vs. Taft School | May 10 | 4:00 PM | Home | 8 - 10 | Home | |
| Varsity Crew | @ Litchfield Hills Rowing Club | May 11 | 10:00 AM | Litchfield Hills Rowing Club - Boathouse | - | Away | |
| Girl's Varsity Lacrosse | vs. Rumsey Hall Girls Lacrosse Invitational | May 11 | 10:30 AM | Home | - | Home | |
| Varsity B Tennis | vs. Washington Montessori School (WMS) | May 13 | 3:00 PM | Home | 7 - 2 | Home | |
| Varsity Softball | vs. Renbrook School | May 14 | 3:45 PM | Home | 11 - 9 | Home | |
| Varsity B Baseball | vs. Renbrook School | May 14 | 3:45 PM | Home | 9 - 14 | Home | |
| Girl's Varsity B Lacrosse | @ Ethel Walker School | May 14 | 4:00 PM | Ethel Walker School | 1 - 10 | Away | |
| Girl's Varsity Lacrosse | @ Indian Mountain School | May 14 | 4:00 PM | Indian Mountain School | 5 - 15 | Away | |
| Boy's Varsity B Lacrosse | vs. Trinity Pawling School | May 14 | 4:00 PM | Home | 2 - 7 | Home | |
| Varsity Baseball | vs. Kent School | May 14 | 4:15 PM | Home | 11 - 2 | Home | |
| Varsity A Tennis | @ Kent School | May 15 | 3:00 PM | Kent School | - | Away | Cancelled |
| Varsity Crew | @ Lower Boat Regatta | May 15 | 3:00 PM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity Softball | @ Indian Mountain School | May 15 | 3:15 PM | Indian Mountain School | - | Away | Cancelled |
| Girl's Varsity Lacrosse | vs. Canterbury School | May 15 | 3:15 PM | Home | 11 - 3 | Home | |
| Boy's Varsity B Lacrosse | @ Hopkins School | May 15 | 3:30 PM | Hopkins School | 2 - 5 | Away | |
| Varsity B Baseball | @ Berkshire Waldorf School | May 15 | 3:45 PM | Berkshire Waldorf School | 8 - 9 | Away | |
| Varsity B Tennis | vs. Mizzentop | May 15 | 3:45 PM | Home | 7 - 1 | Home | |
| Girl's Varsity B Lacrosse | @ Berkshire Waldorf School | May 17 | 3:30 PM | Berkshire Waldorf School | 10 - 10 | Away | |
| Girl's Varsity Lacrosse | @ Taft School | May 20 | 4:00 PM | Home | 7 - 5 | Away | |
| Varsity B Tennis | vs. Dutchess Day School | May 21 | 3:45 PM | Home | 8 - 1 | Home | |
| Girl's Varsity B Lacrosse | vs. Dutchess Day School | May 21 | 3:45 PM | Home | 9 - 1 | Home | |
| Varsity Baseball | @ Avon Old Farms School | May 21 | 4:00 PM | Avon Old Farms School | 5 - 3 | Away | |
| Varsity A Tennis | @ Indian Mountain School | May 21 | 4:00 PM | Indian Mountain School | 2 - 7 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | May 21 | 4:00 PM | Home | 4 - 6 | Home | |
| Varsity Softball | vs. Indian Mountain School | May 22 | 3:15 PM | Home | 12 - 1 | Home | |
| Varsity Baseball | vs. Indian Mountain School | May 22 | 3:15 PM | Home | 13 - 0 | Home | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | May 22 | 3:15 PM | Home | 7 - 7 | Home | |
| Varsity B Baseball | @ Renbrook School | May 22 | 3:30 PM | Renbrook School | 1 - 15 | Away | |
| Varsity A Tennis | vs. Salisbury School | May 22 | 3:30 PM | Home | 7 - 0 | Home | |
| Boy's Varsity B Lacrosse | @ Dutchess Day School | May 22 | 3:30 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Tennis | @ Indian Mountain School | May 22 | 3:45 PM | Home | 6 - 4 | Away | |
| Girl's Varsity Lacrosse | @ Rectory School | May 22 | 4:00 PM | Ethel Walker School | 7 - 7 | Away | |
| Boy's Varsity Lacrosse | @ Indian Mountain School | May 22 | 4:30 PM | Indian Mountain School | 4 - 8 | Away | |
| No events found. | |||||||
| Team | Opponent | Date | Time | Location | Result | Advantage | Status |
|---|---|---|---|---|---|---|---|
| Boy's Varsity Soccer | vs. Trinity Pawling School | Sep 21 | 3:15 PM | Home | 11 - 0 | Home | |
| Varsity Volleyball | vs. Miss Porter's School | Sep 21 | 3:15 PM | Home | 3 - 0 | Home | |
| Varsity Field Hockey | @ Westminster School | Sep 21 | 3:15 PM | Westminster School | 1 - 0 | Away | |
| Blue Dog Bikes - Racing Team | @ TBD | Sep 21 | 3:30 PM | Kent School | - | Away | |
| Varsity B Volleyball | @ Oakwood Friends School | Sep 21 | 3:30 PM | Oakwood Friends School | 2 - 1 | Away | |
| Girl's Varsity Soccer | vs. Renbrook School | Sep 21 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity Cross Country | @ Rhino Run - Taft School Invitational | Sep 21 | 4:00 PM | Taft School | - | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Sep 23 | 3:15 PM | Home | 3 - 0 | Home | |
| Varsity Volleyball | @ Berkshire School | Sep 23 | 3:30 PM | Berkshire School | 0 - 3 | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Sep 23 | 3:30 PM | Indian Mountain School | 7 - 5 | Away | |
| Varsity B Soccer | vs. Mizzentop | Sep 23 | 4:00 PM | Home | 3 - 9 | Home | |
| Boy's Varsity Soccer | vs. Taft School | Sep 23 | 4:00 PM | Home | 7 - 7 | Home | |
| Girl's Varsity Soccer | @ Millbrook School | Sep 23 | 4:15 PM | Millbrook School | 8 - 2 | Away | |
| Varsity Football | @ Williston Northampton School | Sep 24 | 10:00 AM | Williston Northampton School | - | Away | |
| Girl's Varsity Soccer | vs. Canterbury School | Sep 24 | 2:30 PM | Home | 9 - 1 | Home | |
| Boy's Varsity Soccer | vs. Avon Old Farms School | Sep 28 | 3:15 PM | Home | 8 - 1 | Home | |
| Varsity Volleyball | vs. Choate Rosemary Hall | Sep 28 | 3:15 PM | Home | 3 - 1 | Home | |
| Blue Dog Bikes - Racing Team | @ TBD | Sep 28 | 3:30 PM | South Kent School | - | Away | |
| Varsity Field Hockey | @ Berkshire School | Sep 28 | 3:30 PM | Berkshire School | 1 - 3 | Away | |
| Girl's Varsity Soccer | vs. Foote School | Sep 28 | 3:45 PM | Home | 8 - 1 | Home | |
| Varsity B Field Hockey | vs. Mizzentop | Sep 28 | 3:45 PM | Home | 0 - 0 | Home | |
| Varsity B Volleyball | @ Miss Porter's School | Sep 28 | 4:00 PM | Miss Porter's School | 1 - 2 | Away | |
| Girl's Varsity Soccer | @ Hotchkiss School | Sep 29 | 4:15 PM | Hotchkiss School | - | Away | Cancelled |
| Varsity Volleyball | @ Ethel Walker School | Sep 30 | 3:00 PM | Ethel Walker School | 0 - 3 | Away | |
| Varsity Cross Country | vs. Indian Mountain School | Sep 30 | 3:15 PM | Home | 29 - 27 | Home | |
| Junior Blue Soccer | @ TBD | Sep 30 | 3:30 PM | Dutchess Day School | - | Away | |
| Varsity B Soccer | @ TBD | Sep 30 | 3:30 PM | Dutchess Day School | - | Away | |
| Girl's Varsity Soccer | @ Ethel Walker School | Sep 30 | 4:00 PM | Ethel Walker School | 5 - 1 | Away | |
| Varsity Football | @ Avon Old Farms School | Sep 30 | 4:00 PM | Avon Old Farms School | 28 - 0 | Away | |
| Boy's Varsity Soccer | vs. Frederick Gunn School | Sep 30 | 4:00 PM | Rumsey Hall School | 6 - 3 | Home | |
| Varsity Field Hockey | @ Miss Porter's School | Oct 1 | 3:00 PM | Miss Porter's School | 0 - 0 | Away | |
| Varsity B Soccer | @ Sherman Middle School | Oct 4 | 3:45 PM | Sherman Middle School | 5 - 0 | Away | |
| Junior Blue Soccer | @ Dutchess Day School | Oct 4 | 4:00 PM | Dutchess Day School | 4 - 2 | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 4 | 4:00 PM | Dutchess Day School | 0 - 1 | Away | |
| Varsity Volleyball | vs. Kent School | Oct 5 | 3:15 PM | Home | 1 - 3 | Home | |
| Girl's Varsity Soccer | @ Canterbury School | Oct 5 | 3:15 PM | Canterbury School | - | Away | Cancelled |
| Boy's Varsity Soccer | vs. Hotchkiss School | Oct 5 | 3:15 PM | Home | 5 - 1 | Home | |
| Varsity Field Hockey | @ Canterbury School | Oct 5 | 3:15 PM | Canterbury School | - | Away | Cancelled |
| Blue Dog Bikes - Racing Team | @ TBD | Oct 5 | 3:30 PM | Hotchkiss School | - | Away | Cancelled |
| Varsity B Volleyball | vs. Oakwood Friends School | Oct 5 | 3:30 PM | Home | 3 - 1 | Home | |
| Junior Blue Soccer | vs. Mizzentop | Oct 5 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity Cross Country | vs. Indian Mountain School | Oct 5 | 3:45 PM | Home | 40 - 24 | Home | |
| Varsity Football | @ Fessenden School | Oct 6 | 3:30 PM | Fessenden School | 8 - 20 | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 7 | 3:30 PM | Indian Mountain School | 2 - 1 | Away | |
| Varsity B Soccer | @ Mizzentop | Oct 7 | 4:00 PM | Trinity Pawling School | 3 - 2 | Away | |
| Boy's Varsity Soccer | vs. Millbrook School | Oct 7 | 4:30 PM | Home | 7 - 1 | Home | |
| Girl's Varsity Soccer | @ Miss Porter's School | Oct 8 | 11:00 AM | Miss Porter's School | 8 - 0 | Away | |
| Varsity Volleyball | vs. Hopkins School | Oct 8 | 2:30 PM | Home | 3 - 1 | Home | |
| Varsity Field Hockey | vs. Loomis Chaffee | Oct 8 | 2:30 PM | Home | 7 - 0 | Home | |
| Varsity B Soccer | vs. Dutchess Day School | Oct 11 | 3:45 PM | Home | 1 - 7 | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 11 | 3:45 PM | Home | 0 - 0 | Home | |
| Varsity Volleyball | @ Kent School | Oct 11 | 4:00 PM | Kent School | 2 - 3 | Away | |
| Varsity Field Hockey | vs. Hotchkiss School | Oct 12 | 3:00 PM | Home | 3 - 0 | Home | |
| Varsity Volleyball | vs. Hotchkiss School | Oct 12 | 3:15 PM | Home | 2 - 3 | Home | |
| Varsity B Volleyball | @ Forman School | Oct 12 | 3:15 PM | Forman School | 2 - 3 | Away | |
| Girl's Varsity Soccer | vs. Miss Porter's School | Oct 12 | 3:15 PM | Home | 4 - 1 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Oct 12 | 3:15 PM | Home | 2 - 6 | Home | |
| Boy's Varsity Soccer | @ Kent School | Oct 12 | 3:15 PM | Kent School | 6 - 3 | Away | |
| Varsity Football | vs. Avon Old Farms School | Oct 12 | 3:30 PM | Home | 26 - 8 | Home | |
| Blue Dog Bikes - Racing Team | @ TBD | Oct 12 | 3:30 PM | Trinity Pawling School | - | Away | |
| Varsity Cross Country | @ Millbrook School | Oct 12 | 3:30 PM | Millbrook School | - | Away | |
| Junior Blue Soccer | vs. TBD | Oct 13 | 3:00 PM | Playing Fields - Pavek Athletic Field | - | Home | Cancelled |
| Varsity B Soccer | vs. Washington Montessori School (WMS) | Oct 13 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 4 - 7 | Home | |
| Girl's Varsity Soccer | @ Washington Montessori School (WMS) | Oct 13 | 3:45 PM | Washington Montessori School (WMS) | 5 - 3 | Away | |
| Boy's Varsity Soccer | vs. Indian Mountain School | Oct 13 | 4:00 PM | Home | 4 - 6 | Home | |
| Varsity Football | vs. TBD | Oct 15 | 2:30 PM | Home | - | Home | |
| Varsity Volleyball | vs. Taft School | Oct 15 | 2:30 PM | Home | 3 - 1 | Home | |
| Girl's Varsity Soccer | vs. Westminster School | Oct 15 | 2:30 PM | Home | 5 - 0 | Home | |
| Varsity Field Hockey | vs. Canterbury School | Oct 15 | 2:30 PM | Home | 1 - 0 | Home | |
| Varsity B Soccer | @ Trinity Pawling School | Oct 18 | 4:00 PM | Trinity Pawling School | 0 - 7 | Away | |
| Varsity B Soccer | vs. Indian Mountain School | Oct 19 | 3:15 PM | Home | 1 - 5 | Home | |
| Varsity B Volleyball | vs. Hopkins School | Oct 19 | 3:15 PM | Home | 2 - 3 | Home | |
| Girl's Varsity Soccer | @ Kingswood-Oxford School | Oct 19 | 3:30 PM | Kingswood-Oxford School | - | Away | Cancelled |
| Varsity Football | vs. Kingswood-Oxford School | Oct 19 | 3:30 PM | Home | 28 - 6 | Home | |
| Blue Dog Bikes - Racing Team | @ TBD | Oct 19 | 3:30 PM | Berkshire School | - | Away | |
| Varsity B Field Hockey | vs. Mizzentop | Oct 19 | 3:45 PM | Home | - | Home | Cancelled |
| Junior Blue Soccer | @ Mizzentop | Oct 19 | 4:00 PM | Trinity Pawling School | 3 - 7 | Away | |
| Junior Red Soccer | @ Washington Montessori School (WMS) | Oct 20 | 3:45 PM | Washington Montessori School (WMS) | 0 - 7 | Away | |
| Junior Blue Soccer | @ Renbrook School | Oct 20 | 4:00 PM | Renbrook School | 2 - 5 | Away | |
| Girl's Varsity Soccer | vs. Kent Center School | Oct 20 | 4:00 PM | Playing Fields - Seibert Memorial Field | 5 - 0 | Home | |
| Varsity B Soccer | vs. Trinity Pawling School | Oct 25 | 3:45 PM | Home | 0 - 10 | Home | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 25 | 3:45 PM | Home | 1 - 2 | Home | |
| Varsity Football | @ Hopkins School | Oct 25 | 4:00 PM | Hopkins School | 22 - 0 | Away | |
| Girl's Varsity Soccer | vs. Berkshire School | Oct 26 | 3:15 PM | Home | 2 - 2 | Home | |
| Boy's Varsity Soccer | vs. Choate Rosemary Hall | Oct 26 | 3:15 PM | Home | 7 - 0 | Home | |
| Varsity Volleyball | @ Westover School | Oct 26 | 3:15 PM | Westover School | 3 - 0 | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Oct 26 | 3:30 PM | Indian Mountain School | 3 - 4 | Away | |
| Blue Dog Bikes - Racing Team | @ TBD | Oct 26 | 3:30 PM | Indian Mountain School | - | Away | |
| Varsity Field Hockey | vs. Renbrook School | Oct 26 | 3:45 PM | Home | 5 - 0 | Home | |
| Varsity Cross Country | @ Indian Mountain School | Oct 26 | 4:15 PM | Indian Mountain School | - | Away | |
| Varsity B Volleyball | @ Hotchkiss School | Oct 26 | 4:15 PM | Hotchkiss School | 0 - 3 | Away | |
| Varsity B Field Hockey | @ Mizzentop | Oct 27 | 4:00 PM | Trinity Pawling School | 0 - 2 | Away | |
| Junior Blue Soccer | vs. Mizzentop | Oct 27 | 4:00 PM | Home | 3 - 5 | Home | |
| Varsity B Soccer | vs. Renbrook School | Oct 27 | 4:00 PM | Home | 0 - 5 | Home | |
| Boy's Varsity Soccer | vs. Foote School | Oct 27 | 4:00 PM | Home | - | Home | Cancelled |
| Girl's Varsity Soccer | @ Indian Mountain School | Oct 28 | 3:30 PM | Indian Mountain School | 3 - 9 | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Oct 28 | 3:30 PM | Home | 3 - 1 | Home | |
| Varsity Volleyball | @ Indian Mountain School | Oct 28 | 3:30 PM | Indian Mountain School | 1 - 3 | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 28 | 3:45 PM | Dutchess Day School | 0 - 3 | Away | |
| Varsity Cross Country | @ Dutchess Day School | Oct 28 | 3:45 PM | Dutchess Day School | - | Away | |
| Varsity Field Hockey | vs. Taft School | Oct 28 | 4:00 PM | Home | 5 - 0 | Home | |
| Varsity Field Hockey | @ Loomis Chaffee | Oct 29 | 2:30 PM | Loomis Chaffee | 5 - 0 | Away | |
| Varsity Football | @ Eaglebrook School | Oct 29 | 2:30 PM | Eaglebrook School | 6 - 30 | Away | |
| Varsity B Soccer | @ Dutchess Day School | Nov 1 | 3:45 PM | Dutchess Day School | 2 - 7 | Away | |
| Girl's Varsity Soccer | vs. Ethel Walker School | Nov 2 | 3:00 PM | Rumsey Hall School | 4 - 1 | Home | |
| Blue Dog Bikes - Racing Team | @ TBD | Nov 2 | 3:00 PM | Home | - | Away | |
| Varsity Field Hockey | vs. Westminster School | Nov 2 | 3:15 PM | Home | 5 - 0 | Home | |
| Boy's Varsity Soccer | @ Westminster School | Nov 2 | 3:15 PM | Westminster School | 7 - 1 | Away | |
| Varsity Cross Country | @ Kingswood-Oxford School | Nov 2 | 3:30 PM | Kingswood-Oxford School | - | Away | Cancelled |
| Varsity Volleyball | @ Choate Rosemary Hall | Nov 2 | 3:30 PM | Choate Rosemary Hall | 3 - 0 | Away | |
| Girl's Varsity Soccer | vs. Sherman Middle School | Nov 3 | 3:15 PM | Home | 6 - 0 | Home | |
| Junior Blue Soccer | vs. Dutchess Day School | Nov 3 | 3:45 PM | Home | 6 - 2 | Home | |
| Junior Red Soccer | vs. TBD | Nov 3 | 3:45 PM | Home | - | Home | Rescheduled to Nov 7 |
| Varsity B Field Hockey | vs. Mizzentop | Nov 3 | 3:45 PM | Home | 0 - 2 | Home | |
| Varsity Volleyball | @ Taft School | Nov 3 | 4:00 PM | Taft School | 3 - 1 | Away | |
| Boy's Varsity Soccer | @ Avon Old Farms School | Nov 3 | 4:00 PM | Avon Old Farms School | 3 - 3 | Away | |
| Girl's Varsity Soccer | vs. Sherman Middle School | Nov 4 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity B Soccer | vs. Sherman Middle School | Nov 4 | 3:30 PM | Home | 6 - 1 | Home | |
| Varsity Field Hockey | vs. Frederick Gunn School | Nov 4 | 3:45 PM | Home | 2 - 0 | Home | |
| Varsity B Volleyball | @ Hopkins School | Nov 4 | 4:15 PM | Hopkins School | 3 - 0 | Away | |
| Boy's Varsity Soccer | @ Eaglebrook School | Nov 5 | 9:00 AM | Eaglebrook School | - | Away | |
| Girl's Varsity Soccer | @ Indian Mountain School | Nov 5 | 10:30 AM | Indian Mountain School | 0 - 5 | Away | |
| Varsity Volleyball | vs. Rick Spooner Volleyball Classic | Nov 5 | 2:00 PM | Home | - | Home | |
| Junior Red Soccer | vs. Washington Montessori School (WMS) | Nov 7 | 3:30 PM | Home | 2 - 2 | Home | |
| Varsity B Field Hockey | @ Renbrook School | Nov 8 | 3:15 PM | Renbrook School | 1 - 6 | Away | |
| Varsity B Volleyball | vs. Forman School | Nov 8 | 4:15 PM | Home | 3 - 1 | Home | |
| Varsity Football | @ Brunswick School | Nov 9 | 3:00 PM | Brunswick School | 16 - 8 | Away | |
| Girl's Varsity Soccer | @ Westminster School | Nov 9 | 3:00 PM | Westminster School | 5 - 0 | Away | |
| Boy's Varsity Soccer | vs. Salisbury School | Nov 9 | 3:00 PM | Home | 5 - 2 | Home | |
| Varsity Field Hockey | @ Hotchkiss School | Nov 9 | 3:00 PM | Hotchkiss School | 4 - 0 | Away | |
| Varsity B Volleyball | vs. TBD | Nov 9 | 3:15 PM | Home | - | Home | Rescheduled to Nov 8 |
| Varsity Volleyball | @ Kingswood-Oxford School | Nov 9 | 3:30 PM | Kingswood-Oxford School | 2 - 1 | Away | |
| Varsity Cross Country | vs. Washington Montessori School (WMS) | Nov 9 | 3:30 PM | Home | - | Home | |
| Boy's Varsity Soccer | @ Indian Mountain School | Nov 10 | 6:30 PM | Hotchkiss School | 3 - 2 | Away | |
| Varsity Cross Country | @ Indian Mountain School | Nov 11 | 2:45 PM | Indian Mountain School | - | Away | |
| Girl's Varsity Soccer | vs. Indian Mountain School | Nov 11 | 2:45 PM | Home | 5 - 7 | Home | |
| Varsity B Soccer | @ Indian Mountain School | Nov 11 | 2:45 PM | Indian Mountain School | 0 - 2 | Away | |
| Junior Blue Soccer | vs. Indian Mountain School | Nov 11 | 2:45 PM | Home | 7 - 5 | Home | |
| Varsity Volleyball | vs. Indian Mountain School | Nov 11 | 3:00 PM | Home | 0 - 3 | Home | |
| Varsity B Volleyball | @ Indian Mountain School | Nov 11 | 3:00 PM | Indian Mountain School | 3 - 1 | Away | |
| Girl's Varsity Ice Hockey | @ Greenwich Country Day | Dec 2 | 6:00 PM | Greenwich Skating Club | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Rectory School | Dec 3 | 12:30 PM | Pomfret School | 6 - 0 | Away | |
| Girl's Varsity Basketball | @ Kent Center School | Dec 6 | 3:30 PM | Kent Center School | 26 - 17 | Away | |
| Boy's Varsity Ice Hockey | vs. Westminster School | Dec 7 | 3:30 PM | Home | 7 - 3 | Home | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Dec 8 | 12:00 PM | Home | 2 - 8 | Home | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Dec 8 | 3:30 PM | Home | 8 - 3 | Home | |
| Boy's Varsity B Basketball | vs. Kent Center School | Dec 8 | 4:00 PM | Home | 18 - 36 | Home | |
| Boy's Varsity Ice Hockey | vs. Avon Old Farms School | Dec 10 | 2:30 PM | Home | 0 - 7 | Home | |
| Boy's Varsity Ice Hockey | @ NCCS (New Canaan Country School) | Jan 7 | 12:00 PM | Upland Country Day School | 4 - 2 | Away | |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 7 | 4:15 PM | Upland Country Day School | 4 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ Maine Mariners | Jan 8 | 9:45 AM | Upland Country Day School | 10 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ NCCS (New Canaan Country School) | Jan 8 | 1:15 PM | Upland Country Day School | 8 - 3 | Away | |
| Girl's Varsity B Basketball | vs. Renbrook School | Jan 10 | 3:45 PM | Home | 10 - 16 | Home | |
| Boy's Varsity B Basketball | @ Dutchess Day School | Jan 10 | 3:45 PM | Dutchess Day School | 27 - 20 | Away | |
| Girl's Varsity Ice Hockey | @ Kent School | Jan 11 | 1:45 PM | Kent School | 5 - 3 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 11 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Jan 11 | 3:15 PM | Home | 62 - 57 | Home | |
| Girl's Varsity Basketball | @ Kingswood-Oxford School | Jan 11 | 3:30 PM | Kingswood-Oxford School | 21 - 30 | Away | |
| Boy's Varsity Ice Hockey | vs. Trinity Pawling School | Jan 11 | 3:30 PM | Home | - | Home | Cancelled |
| Girl's Varsity Basketball | @ Sherman Middle School | Jan 12 | 3:30 PM | Sherman Middle School | 37 - 18 | Away | |
| Boy's Varsity B Basketball | vs. Sherman Middle School | Jan 12 | 3:30 PM | Home | 31 - 39 | Home | |
| Boy's Varsity Basketball | vs. Brunswick School | Jan 12 | 4:00 PM | Home | 44 - 28 | Home | |
| Girl's Varsity Ice Hockey | vs. Indian Mountain School | Jan 13 | 2:30 PM | Lufkin Rink - Rink - 2600 | 4 - 0 | Home | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Jan 13 | 2:45 PM | Indian Mountain School | 17 - 24 | Away | |
| Varsity B Ice Hockey | @ Eaglebrook School | Jan 13 | 4:00 PM | Eaglebrook School | 5 - 3 | Away | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Jan 13 | 4:00 PM | Home | 8 - 2 | Home | |
| Girl's Varsity Basketball | vs. Choate Rosemary Hall | Jan 14 | 2:30 PM | Home | 22 - 19 | Home | |
| Girls Varsity B Ice Hockey | vs. Shoreline Sharks | Jan 15 | 11:00 AM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity B Basketball | vs. Trinity Pawling School | Jan 17 | 3:30 PM | Home | 32 - 25 | Home | |
| Boy's Varsity Basketball | vs. Canterbury School | Jan 18 | 2:30 PM | Home | 60 - 40 | Home | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Jan 18 | 2:30 PM | Home | 8 - 1 | Home | |
| Varsity Ski Team | @ Washington Montessori School (WMS) | Jan 18 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Indian Mountain School | Jan 18 | 3:15 PM | Home | 28 - 31 | Home | |
| Boy's Varsity Ice Hockey | @ Kent School | Jan 18 | 6:30 PM | Kent School | 10 - 0 | Away | |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Jan 19 | 3:30 PM | Home | 22 - 10 | Home | |
| Winter Volleyball | @ Dutchess Day School | Jan 19 | 3:45 PM | Dutchess Day School | 0 - 3 | Away | |
| Boy's Varsity B Basketball | @ Kent Center School | Jan 19 | 4:00 PM | Kent Center School | 21 - 37 | Away | |
| Girl's Varsity Basketball | vs. Kent Center School | Jan 19 | 4:00 PM | Home | 22 - 9 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Jan 20 | 3:30 PM | Catamount Ski Area | - | Away | Cancelled |
| Boy's Varsity Basketball | @ Kent School | Jan 20 | 4:00 PM | Kent School | 49 - 42 | Away | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 20 | 4:00 PM | Home | 4 - 3 | Home | |
| Girl's Varsity Ice Hockey | @ Wild Rams | Jan 21 | 12:00 PM | Upland Country Day School | 2 - 8 | Away | |
| Girl's Varsity Ice Hockey | @ Lower Merion Girls Hockey | Jan 21 | 4:15 PM | Upland Country Day School | 7 - 2 | Away | |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 21 | 4:30 PM | Cardigan Mountain School | 3 - 2 | Away | |
| Girl's Varsity Ice Hockey | @ Upland Country Day School | Jan 22 | 8:00 AM | Upland Country Day School | 2 - 7 | Away | |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 22 | 9:00 AM | Cardigan Mountain School | 2 - 9 | Away | |
| Girl's Varsity Ice Hockey | @ Lower Merion Girls Hockey | Jan 22 | 12:00 PM | Upland Country Day School | 3 - 1 | Away | |
| Girl's Varsity B Basketball | vs. Ethel Walker School | Jan 24 | 4:00 PM | Home | 4 - 32 | Home | |
| Girl's Varsity Basketball | vs. Canterbury School | Jan 25 | 2:30 PM | Home | 44 - 29 | Home | |
| Boy's Varsity Ice Hockey | vs. Berkshire School | Jan 25 | 2:30 PM | Home | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 25 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | Cancelled |
| Boy's Varsity B Basketball | vs. Oakwood Friends School | Jan 25 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity B Ice Hockey | vs. Indian Mountain School | Jan 25 | 4:15 PM | Home | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | @ Canterbury School | Jan 25 | 4:30 PM | Canterbury School | 0 - 4 | Away | |
| Boy's Varsity Basketball | @ Avon Old Farms School | Jan 25 | 4:30 PM | Avon Old Farms School | - | Away | Cancelled |
| Boy's Varsity B Basketball | @ Sherman Middle School | Jan 26 | 3:30 PM | Home | 20 - 42 | Away | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Jan 26 | 3:30 PM | Washington Montessori School (WMS) | 8 - 22 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Jan 26 | 3:45 PM | Home | 1 - 2 | Home | |
| Boy's Jr. Blue Basketball | @ Renbrook School | Jan 26 | 3:45 PM | Renbrook School | 21 - 42 | Away | |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Jan 27 | 2:15 PM | Hotchkiss School | 5 - 0 | Away | |
| Boy's Varsity Basketball | vs. Indian Mountain School | Jan 27 | 3:15 PM | Home | 50 - 39 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Jan 27 | 3:30 PM | Catamount Ski Area | - | Away | |
| Girl's Varsity Ice Hockey | vs. Kent School | Jan 28 | 2:00 PM | Home | 0 - 1 | Home | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Jan 30 | 3:30 PM | Washington Montessori School (WMS) | 32 - 20 | Away | |
| Boy's Varsity Ice Hockey | @ Brunswick School | Jan 30 | 3:45 PM | Brunswick School - Hartong Rink | 4 - 3 | Away | |
| Boy's Varsity B Basketball | vs. Mizzentop | Jan 30 | 4:00 PM | Home | 40 - 16 | Home | |
| Boy's Varsity Basketball | vs. Trinity Pawling School | Jan 30 | 4:30 PM | Home | 52 - 31 | Home | |
| Girls Varsity B Ice Hockey | vs. Millbrook School | Feb 1 | 2:30 PM | Home | 2 - 8 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 1 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Hotchkiss School | Feb 1 | 3:30 PM | Home | 35 - 20 | Home | |
| Boy's Varsity Basketball | vs. Taft School | Feb 1 | 3:30 PM | Home | 65 - 32 | Home | |
| Boy's Varsity B Basketball | @ Hopkins School | Feb 1 | 3:45 PM | Hopkins School | 18 - 38 | Away | |
| Varsity B Ice Hockey | @ Taft School | Feb 1 | 4:30 PM | Taft School | 3 - 0 | Away | |
| Boy's Jr. Blue Basketball | vs. Sherman Middle School | Feb 2 | 3:30 PM | Home | 31 - 13 | Home | |
| Girl's Varsity B Basketball | @ Renbrook School | Feb 2 | 3:45 PM | Renbrook School | 10 - 42 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Feb 2 | 3:45 PM | Home | 0 - 3 | Home | |
| Girl's Varsity Ice Hockey | vs. Taft School | Feb 2 | 4:15 PM | Home | 3 - 7 | Home | |
| Boy's Varsity Ice Hockey | vs. Connecticut Chiefs '09 AAA | Feb 2 | 7:15 PM | Home | 2 - 3 | Home | |
| Varsity B Ice Hockey | @ Indian Mountain School | Feb 3 | 3:00 PM | Hotchkiss School | 5 - 2 | Away | |
| Boy's Varsity B Basketball | @ Indian Mountain School | Feb 3 | 3:00 PM | Home | 25 - 17 | Away | |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 3 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 8 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Varsity B Ice Hockey | vs. Frederick Gunn School | Feb 8 | 3:30 PM | Home | 9 - 3 | Home | |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Feb 8 | 3:30 PM | Home | 33 - 21 | Home | |
| Boy's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 8 | 3:30 PM | Home | 33 - 50 | Home | |
| Girl's Varsity Ice Hockey | @ Hotchkiss School | Feb 8 | 4:30 PM | Hotchkiss School | 2 - 1 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Feb 9 | 3:45 PM | Home | 0 - 3 | Home | |
| Boy's Jr. Blue Basketball | vs. Mizzentop | Feb 9 | 4:00 PM | Home | 30 - 29 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 10 | 2:30 PM | Home | 5 - 2 | Home | |
| Boy's Varsity Basketball | @ Salisbury School | Feb 10 | 3:00 PM | Salisbury School | 48 - 25 | Away | |
| Varsity Ski Team | @ Indian Mountain School | Feb 10 | 3:30 PM | Catamount Ski Area | - | Away | |
| Girl's Varsity B Basketball | @ Hotchkiss School | Feb 10 | 4:15 PM | Hotchkiss School | 10 - 44 | Away | |
| Girl's Varsity Ice Hockey | vs. Berkshire School | Feb 10 | 4:15 PM | Home | 5 - 4 | Home | |
| Boy's Varsity Ice Hockey | vs. Kent School | Feb 10 | 5:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | vs. CT GC Hockey | Feb 10 | 7:30 PM | Home | 3 - 2 | Home | |
| Boy's Varsity B Basketball | @ Maplebrook School Boys Basketball Tournament | Feb 11 | 10:00 AM | Maplebrook School | - | Away | |
| Boy's Varsity B Basketball | @ Maplebrook School | Feb 11 | 10:30 AM | Home | 42 - 39 | Away | |
| Boy's Varsity B Basketball | vs. Woodhall School | Feb 11 | 12:30 PM | Home | 34 - 52 | Home | |
| Boy's Varsity Basketball | @ Indian Mountain School | Feb 11 | 1:00 PM | Indian Mountain School | 73 - 63 | Away | |
| Girl's Varsity Basketball | @ Canterbury School | Feb 11 | 1:30 PM | Canterbury School | 45 - 21 | Away | |
| Girl's Varsity Ice Hockey | vs. Westminster School | Feb 11 | 2:30 PM | Home | 5 - 3 | Home | |
| Boy's Jr. Blue Basketball | @ Sherman Middle School | Feb 14 | 3:30 PM | Sherman Middle School | 23 - 4 | Away | |
| Boy's Varsity B Basketball | @ Trinity Pawling School | Feb 14 | 3:45 PM | Trinity Pawling School | 34 - 33 | Away | |
| Boy's Varsity Ice Hockey | @ Brunswick School | Feb 14 | 3:45 PM | Brunswick School - Hartong Rink | 3 - 5 | Away | |
| Girl's Varsity Ice Hockey | vs. Canterbury School | Feb 15 | 2:30 PM | Home | 3 - 7 | Home | |
| Girl's Varsity Basketball | @ Indian Mountain School | Feb 15 | 3:00 PM | Indian Mountain School | 28 - 36 | Away | |
| Girl's Varsity B Basketball | @ Ethel Walker School | Feb 15 | 3:30 PM | Ethel Walker School | - | Away | Cancelled |
| Varsity Ski Team | @ Washington Montessori School (WMS) | Feb 15 | 3:30 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity Basketball | vs. Hopkins School | Feb 15 | 3:30 PM | Home | 46 - 21 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 15 | 4:15 PM | Home | 4 - 1 | Home | |
| Boy's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 16 | 3:30 PM | Washington Montessori School (WMS) | 35 - 50 | Away | |
| Girl's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 16 | 3:30 PM | Home | 4 - 18 | Home | |
| Winter Volleyball | @ Dutchess Day School | Feb 16 | 3:45 PM | Dutchess Day School | 1 - 2 | Away | |
| Boy's Jr. Blue Basketball | @ TBD | Feb 16 | 4:00 PM | Mizzentop | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | @ Mizzentop | Feb 16 | 4:00 PM | Mizzentop | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Feb 17 | 2:30 PM | Home | 40 - 38 | Home | |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 17 | 3:30 PM | Home | 9 - 2 | Home | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Feb 17 | 4:00 PM | Home | 64 - 32 | Home | |
| Girl's Varsity Basketball | vs. Frederick Gunn School | Feb 17 | 4:15 PM | Home | 32 - 20 | Home | |
| Girl's Varsity Ice Hockey | vs. Danbury Hat Tricks U14 Girls | Feb 18 | 10:00 AM | Home | 8 - 3 | Home | |
| Girl's Varsity Ice Hockey | vs. Przygocki Cup Girls Ice Hockey Tournament | Feb 18 | 10:00 AM | Home | - | Home | |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Feb 18 | 1:00 PM | Home | 4 - 3 | Home | |
| Boy's Varsity Basketball | @ Westminster School | Feb 18 | 2:30 PM | Westminster School | 78 - 36 | Away | |
| Girl's Varsity Ice Hockey | vs. Shoreline Sharks | Feb 18 | 3:00 PM | Home | 7 - 2 | Home | |
| Girl's Varsity B Basketball | @ Ethel Walker School | Feb 20 | 3:45 PM | Home | 18 - 22 | Away | |
| Boy's Varsity B Basketball | vs. Maplebrook School | Feb 20 | 4:00 PM | Home | - | Home | Cancelled |
| Boy's Varsity Basketball | @ Canterbury School | Feb 20 | 4:15 PM | Canterbury School | 68 - 51 | Away | |
| Boy's Varsity Ice Hockey | vs. Trinity Pawling School | Feb 20 | 4:30 PM | Lufkin Rink - Rink - 2600 | 7 - 0 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 22 | 11:00 AM | Catamount Ski Area | - | Away | |
| Boy's Varsity B Basketball | vs. Indian Mountain School | Feb 22 | 2:30 PM | Home | 26 - 21 | Home | |
| Boy's Varsity Ice Hockey | vs. Salisbury School | Feb 22 | 3:00 PM | Home | 3 - 4 | Home | |
| Boy's Varsity Basketball | vs. Berkshire School | Feb 22 | 3:30 PM | Home | 56 - 36 | Home | |
| Boy's Jr. Blue Basketball | vs. Dutchess Day School | Feb 22 | 4:00 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Varsity B Ice Hockey | vs. Frederick Gunn School | Feb 22 | 4:30 PM | Home | 7 - 3 | Home | |
| Girls Varsity B Ice Hockey | @ Millbrook School | Feb 22 | 4:45 PM | Millbrook School | - | Away | Cancelled |
| Girl's Varsity B Basketball | vs. Sherman Middle School | Feb 23 | 3:30 PM | Home | 7 - 28 | Home | |
| Winter Volleyball | @ Dutchess Day School | Feb 23 | 3:45 PM | Dutchess Day School | 0 - 3 | Away | |
| Boy's Jr. Blue Basketball | vs. Renbrook School | Feb 23 | 3:45 PM | Home | 41 - 54 | Home | |
| Varsity Ski Team | @ Indian Mountain School | Feb 24 | 3:30 PM | Catamount Ski Area | - | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 24 | 3:30 PM | Home | 7 - 2 | Home | |
| Girl's Varsity Ice Hockey | @ Berkshire School | Feb 24 | 4:30 PM | Berkshire School | 2 - 4 | Away | |
| Girl's Varsity Basketball | @ Berkshire School | Feb 24 | 4:30 PM | Berkshire School | 27 - 15 | Away | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 25 | 10:30 AM | Home | - | Home | |
| Boy's Varsity Ice Hockey | vs. Cardigan Mountain School | Feb 25 | 12:00 PM | Home | 2 - 4 | Home | |
| Girl's Varsity Basketball | vs. Ethel Walker School | Feb 25 | 1:30 PM | Home | 34 - 22 | Home | |
| Boy's Varsity B Basketball | vs. Taft School | Feb 25 | 2:30 PM | Home | 33 - 27 | Home | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Feb 25 | 4:30 PM | Home | 4 - 1 | Home | |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 26 | 8:00 AM | Home | 5 - 0 | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 26 | 8:00 AM | Home | - | Home | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Feb 26 | 12:30 PM | Home | 4 - 5 | Home | |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Feb 27 | 6:30 PM | Silo Ridge | 2 - 0 | Away | |
| Boy's Varsity Ice Hockey | vs. CT GC Hockey | Feb 28 | 7:15 PM | Home | 3 - 0 | Home | |
| Boy's Varsity Lacrosse | vs. Hamden Hall | Apr 11 | 4:00 PM | Home | 7 - 6 | Home | |
| Varsity A Tennis | vs. Millbrook School | Apr 11 | 4:30 PM | Home | 8 - 0 | Home | |
| Girl's Varsity Lacrosse | @ Westminster School | Apr 12 | 3:15 PM | Westminster School | - | Away | Cancelled |
| Varsity Baseball | @ Berkshire School | Apr 12 | 3:15 PM | Berkshire School | 21 - 6 | Away | |
| Boy's Varsity Lacrosse | vs. Trinity Pawling School | Apr 12 | 3:15 PM | Home | 15 - 1 | Home | |
| Varsity Softball | vs. Hopkins School | Apr 12 | 3:30 PM | Home | - | Home | Cancelled |
| Girl's Varsity B Lacrosse | vs. Mizzentop | Apr 12 | 3:45 PM | Home | 4 - 15 | Home | |
| Boy's Varsity B Lacrosse | @ Dutchess Day School | Apr 12 | 3:45 PM | Dutchess Day School | 9 - 1 | Away | |
| Varsity Softball | vs. Renbrook School | Apr 13 | 3:45 PM | Home | 7 - 8 | Home | |
| Varsity B Tennis | vs. Mizzentop | Apr 13 | 3:45 PM | Home | 6 - 1 | Home | |
| Varsity B Tennis | vs. Indian Mountain School | Apr 14 | 2:45 PM | Home | 5 - 2 | Home | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | Apr 14 | 3:15 PM | Indian Mountain School | 7 - 5 | Away | |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | Apr 14 | 3:30 PM | Indian Mountain School | 15 - 4 | Away | |
| Girl's Varsity Lacrosse | @ Kent School | Apr 14 | 4:30 PM | Kent School | 8 - 7 | Away | |
| Boy's Varsity B Lacrosse | vs. Trinity Pawling School | Apr 18 | 3:30 PM | Home | 6 - 7 | Home | |
| Varsity Softball | vs. Hamden Hall | Apr 18 | 4:00 PM | Home | 26 - 6 | Home | |
| Girl's Varsity B Lacrosse | @ Ethel Walker School | Apr 18 | 4:00 PM | Ethel Walker School | 9 - 8 | Away | |
| Varsity A Tennis | @ Taft School | Apr 19 | 2:15 PM | Taft School | 8 - 0 | Away | |
| Girl's Varsity Lacrosse | @ Berkshire School | Apr 19 | 3:15 PM | Berkshire School | 9 - 4 | Away | |
| Varsity Baseball | vs. Berkshire School | Apr 19 | 3:15 PM | Home | 9 - 2 | Home | |
| Varsity B Baseball | vs. Kent Center School | Apr 19 | 3:45 PM | Home | - | Home | Cancelled |
| Boy's Varsity Lacrosse | @ Rectory School | Apr 19 | 4:00 PM | Avon Old Farms School | 14 - 5 | Away | |
| Varsity B Tennis | @ Indian Mountain School | Apr 21 | 2:45 PM | Indian Mountain School | 4 - 3 | Away | |
| Varsity Baseball | @ Trinity Pawling School | Apr 21 | 3:15 PM | Trinity Pawling School | 6 - 8 | Away | |
| Girl's Varsity Lacrosse | vs. Hotchkiss School | Apr 21 | 4:00 PM | Home | 9 - 5 | Home | |
| Varsity A Tennis | @ Hotchkiss School | Apr 21 | 4:15 PM | Hotchkiss School | 4 - 3 | Away | |
| Boy's Varsity Lacrosse | vs. Taft School | Apr 21 | 4:15 PM | Home | 12 - 2 | Home | |
| Boy's Varsity Lacrosse | vs. Millbrook School | Apr 24 | 4:15 PM | Home | - | Home | Cancelled |
| Varsity Baseball | @ Canterbury School | Apr 24 | 4:15 PM | Canterbury School | 2 - 12 | Away | |
| Varsity B Tennis | vs. TBD | Apr 25 | 3:45 PM | Home | - | Home | Rescheduled to May 16 |
| Girl's Varsity B Lacrosse | @ Berkshire Waldorf School | Apr 25 | 4:00 PM | Berkshire Waldorf School | 12 - 7 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | Apr 25 | 4:00 PM | Home | 13 - 4 | Home | |
| Boy's Varsity Lacrosse | @ Frederick Gunn School | Apr 26 | 2:30 PM | Home | 12 - 5 | Away | |
| Varsity Crew | @ Salisbury School | Apr 26 | 3:00 PM | Salisbury School | - | Away | |
| Varsity A Tennis | vs. Hotchkiss School | Apr 26 | 3:00 PM | Home | 3 - 4 | Home | |
| Girl's Varsity Lacrosse | @ Indian Mountain School | Apr 26 | 3:15 PM | Indian Mountain School | 6 - 7 | Away | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | Apr 26 | 3:15 PM | Home | - | Home | Cancelled |
| Varsity B Baseball | vs. Renbrook School | Apr 26 | 3:45 PM | Home | 1 - 4 | Home | |
| Varsity Softball | @ Indian Mountain School | Apr 26 | 3:45 PM | Indian Mountain School | 20 - 6 | Away | |
| Varsity B Tennis | @ Indian Mountain School | Apr 28 | 3:15 PM | Home | 3 - 6 | Away | |
| Varsity Baseball | vs. Indian Mountain School | Apr 28 | 3:15 PM | Home | 14 - 2 | Home | |
| Varsity B Baseball | @ Berkshire Waldorf School | Apr 28 | 3:45 PM | Berkshire Waldorf School | 9 - 5 | Away | |
| Varsity A Tennis | vs. Berkshire School | Apr 28 | 4:00 PM | Home | 9 - 0 | Home | |
| Boy's Varsity Lacrosse | @ Hopkins School | Apr 28 | 4:00 PM | Home | 15 - 1 | Away | |
| Girl's Varsity Lacrosse | vs. Loomis Chaffee | Apr 28 | 4:45 PM | Home | 10 - 2 | Home | |
| Boy's Varsity B Lacrosse | @ Hamden Hall | May 2 | 3:00 PM | Hamden Hall | 3 - 5 | Away | |
| Varsity B Baseball | vs. Kent Center School | May 2 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity Lacrosse | vs. Indian Mountain School | May 2 | 4:00 PM | Home | - | Home | Cancelled |
| Varsity B Tennis | vs. Hamden Hall | May 2 | 4:00 PM | Home | 3 - 4 | Home | |
| Varsity A Tennis | @ Indian Mountain School | May 2 | 4:00 PM | Indian Mountain School | 8 - 1 | Away | |
| Girl's Varsity B Lacrosse | @ Mizzentop | May 2 | 4:00 PM | Mizzentop | 4 - 17 | Away | |
| Girl's Varsity Lacrosse | vs. Millbrook School | May 3 | 2:30 PM | Home | 10 - 3 | Home | |
| Varsity B Tennis | vs. Westminster School | May 3 | 3:00 PM | Home | - | Home | Cancelled |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | May 3 | 3:00 PM | Home | 8 - 1 | Home | |
| Boy's Varsity Lacrosse | @ Avon Old Farms School | May 3 | 3:15 PM | Avon Old Farms School | 7 - 2 | Away | |
| Varsity B Baseball | @ Indian Mountain School | May 3 | 3:15 PM | Indian Mountain School | - | Away | Cancelled |
| Varsity Baseball | vs. Brunswick School | May 3 | 3:30 PM | Home | 8 - 7 | Home | |
| Varsity Crew | @ Hotchkiss School | May 3 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity A Tennis | vs. Washington Montessori School (WMS) | May 4 | 3:15 PM | Washington Montessori School (WMS) | 7 - 0 | Home | |
| Varsity Softball | @ Sherman Middle School | May 4 | 3:45 PM | Sherman Middle School | 17 - 8 | Away | |
| Boy's Varsity B Lacrosse | @ Trinity Pawling School | May 4 | 4:00 PM | Trinity Pawling School | - | Away | Cancelled |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | May 5 | 2:45 PM | Indian Mountain School | 6 - 10 | Away | |
| Varsity Crew | @ Choate Rosemary Hall | May 5 | 4:00 PM | Choate Rosemary Hall | - | Away | |
| Varsity A Tennis | vs. Trinity Pawling School | May 6 | 2:30 PM | Home | 7 - 0 | Home | |
| Varsity Baseball | vs. Canterbury School | May 6 | 2:30 PM | Home | 4 - 8 | Home | |
| Girl's Varsity Lacrosse | vs. Westminster School | May 6 | 2:30 PM | Home | - | Home | Cancelled |
| Boy's Varsity Lacrosse | vs. Indian Mountain School | May 6 | 2:30 PM | Home | 12 - 6 | Home | |
| Varsity Crew | @ TBD | May 7 | 8:00 AM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity Softball | @ Foote School | May 9 | 4:00 PM | Foote School | 9 - 10 | Away | |
| Varsity B Tennis | vs. Westminster School | May 10 | 2:45 PM | Home | 2 - 4 | Home | |
| Girl's Varsity Lacrosse | vs. Frederick Gunn School | May 10 | 2:45 PM | Home | 7 - 4 | Home | |
| Varsity B Baseball | vs. Indian Mountain School | May 10 | 3:00 PM | Home | 7 - 6 | Home | |
| Boy's Varsity Lacrosse | vs. Avon Old Farms School | May 10 | 3:00 PM | Home | 4 - 7 | Home | |
| Varsity Crew | @ Berkshire School | May 10 | 3:30 PM | Camp Sloane | - | Away | |
| Varsity Baseball | vs. Masters School (CT) | May 10 | 4:00 PM | Home | 13 - 3 | Home | |
| Girl's Varsity Lacrosse | vs. Mizzentop | May 11 | 3:45 PM | Home | - | Home | Cancelled |
| Varsity Softball | vs. Sherman Middle School | May 11 | 3:45 PM | Home | 16 - 2 | Home | |
| Varsity A Tennis | @ Washington Montessori School (WMS) | May 11 | 3:45 PM | Washington Montessori School (WMS) | 9 - 0 | Away | |
| Girl's Varsity B Lacrosse | vs. Mizzentop | May 11 | 3:45 PM | Home | - | Home | Cancelled |
| Boy's Varsity B Lacrosse | vs. Mizzentop | May 11 | 3:45 PM | Home | 1 - 4 | Home | |
| Varsity A Tennis | @ Frederick Gunn School | May 12 | 3:45 PM | Frederick Gunn School | 8 - 1 | Away | |
| Varsity B Baseball | @ Kent Center School | May 12 | 3:45 PM | Home | 5 - 6 | Away | |
| Varsity Baseball | @ Frederick Gunn School | May 12 | 3:45 PM | Frederick Gunn School | 7 - 8 | Away | |
| Boy's Varsity Lacrosse | @ Taft School | May 12 | 4:00 PM | Home | 8 - 8 | Away | |
| Girl's Varsity Lacrosse | vs. Rumsey Hall Girls Lacrosse Invitational | May 13 | 10:00 AM | Home | - | Home | |
| Varsity Crew | @ Litchfield Hills Rowing Club | May 13 | 10:00 AM | Litchfield Hills Rowing Club - Boathouse | - | Away | |
| Varsity B Baseball | @ Renbrook School | May 16 | 3:45 PM | Renbrook School | 8 - 8 | Away | |
| Varsity Softball | @ Renbrook School | May 16 | 3:45 PM | Renbrook School | 12 - 11 | Away | |
| Varsity B Tennis | vs. Dutchess Day School | May 16 | 3:45 PM | Home | 3 - 4 | Home | |
| Boy's Varsity B Lacrosse | @ Mizzentop | May 16 | 3:45 PM | Trinity Pawling School | 4 - 4 | Away | |
| Girl's Varsity Lacrosse | vs. Indian Mountain School | May 16 | 4:00 PM | Home | 7 - 11 | Home | |
| Girl's Varsity B Lacrosse | vs. Ethel Walker School | May 16 | 4:00 PM | Home | - | Home | Cancelled |
| Varsity Crew | @ Lower Boat Regatta | May 17 | 3:00 PM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity A Tennis | vs. Kent School | May 17 | 3:15 PM | Home | 5 - 4 | Home | |
| Varsity Softball | vs. Indian Mountain School | May 17 | 3:15 PM | Home | 15 - 6 | Home | |
| Boy's Varsity Lacrosse | vs. Hopkins School | May 17 | 3:30 PM | Home | - | Home | Cancelled |
| Varsity Baseball | @ Hamden Hall | May 17 | 3:45 PM | Hamden Hall | 5 - 6 | Away | |
| Girl's Varsity Lacrosse | @ Canterbury School | May 17 | 5:00 PM | Canterbury School | 7 - 1 | Away | |
| Varsity B Tennis | vs. Kent Center School | May 18 | 3:30 PM | Home | 7 - 0 | Home | |
| Varsity B Baseball | vs. Kent Center School | May 19 | 3:45 PM | Home | 7 - 1 | Home | |
| Girl's Varsity B Lacrosse | vs. Berkshire Waldorf School | May 19 | 4:00 PM | Home | 8 - 3 | Home | |
| Varsity B Baseball | vs. Kent Center School | May 22 | 3:45 PM | Home | - | Home | Cancelled |
| Girl's Varsity Lacrosse | vs. Taft School | May 22 | 4:00 PM | Home | 8 - 9 | Home | |
| Varsity A Tennis | vs. Indian Mountain School | May 23 | 3:45 PM | Home | 6 - 3 | Home | |
| Varsity B Tennis | @ Dutchess Day School | May 23 | 3:45 PM | Dutchess Day School | 5 - 4 | Away | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | May 23 | 4:00 PM | Indian Mountain School | 7 - 4 | Away | |
| Varsity Baseball | vs. Avon Old Farms School | May 23 | 4:30 PM | Home | 12 - 2 | Home | |
| Varsity Softball | @ Indian Mountain School | May 24 | 2:45 PM | Indian Mountain School | 16 - 5 | Away | |
| Varsity Baseball | @ Indian Mountain School | May 24 | 2:45 PM | Indian Mountain School | 13 - 1 | Away | |
| Boy's Varsity Lacrosse | @ Indian Mountain School | May 24 | 2:45 PM | Indian Mountain School | 13 - 4 | Away | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | May 24 | 3:15 PM | Home | 13 - 8 | Home | |
| Varsity B Baseball | vs. Berkshire Waldorf School | May 24 | 3:45 PM | Home | 5 - 8 | Home | |
| Boy's Varsity B Lacrosse | vs. Dutchess Day School | May 24 | 3:45 PM | Home | 11 - 5 | Home | |
| Girl's Varsity Lacrosse | @ Rectory School | May 24 | 4:00 PM | Ethel Walker School | 8 - 3 | Away | |
| Varsity A Tennis | @ Salisbury School | May 24 | 4:00 PM | Salisbury School | 8 - 0 | Away | |
| No events found. | |||||||
| Team | Opponent | Date | Time | Location | Result | Advantage | Status |
|---|---|---|---|---|---|---|---|
| Varsity Field Hockey | vs. Westminster School | Sep 22 | 3:15 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 4 - 0 | Home | |
| Girl's Varsity Soccer | @ Renbrook School | Sep 22 | 3:30 PM | Renbrook School | 5 - 1 | Away | |
| Boy's Varsity Soccer | @ Trinity Pawling School | Sep 22 | 3:30 PM | Trinity Pawling School | 10 - 0 | Away | |
| Varsity Volleyball | @ Miss Porter's School | Sep 22 | 3:30 PM | Miss Porter's School | 3 - 0 | Away | |
| Varsity B Volleyball | vs. Oakwood Friends School | Sep 22 | 3:30 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Varsity Cross Country | @ TBD | Sep 22 | 4:00 PM | Taft School | - | Away | Cancelled |
| Varsity Volleyball | @ Berkshire School | Sep 24 | 3:30 PM | Berkshire School | 0 - 3 | Away | |
| Junior Blue Soccer | @ Indian Mountain School | Sep 24 | 3:30 PM | Indian Mountain School | 0 - 7 | Away | |
| Varsity B Volleyball | @ Indian Mountain School | Sep 24 | 3:30 PM | Indian Mountain School | 3 - 0 | Away | |
| Varsity B Soccer | vs. Mizzentop | Sep 24 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Boy's Varsity Soccer | @ Taft School | Sep 24 | 4:00 PM | Taft School | 1 - 1 | Away | |
| Girl's Varsity Soccer | vs. Millbrook School | Sep 24 | 4:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 9 - 1 | Home | |
| Varsity Football | @ Williston Northampton School | Sep 25 | 10:30 AM | Williston Northampton School | - | Away | |
| Girl's Varsity Soccer | vs. Washington Montessori School (WMS) | Sep 27 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 9 - 1 | Home | |
| Varsity Volleyball | vs. Indian Mountain School | Sep 27 | 4:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 2 - 3 | Home | |
| Varsity B Field Hockey | @ Mizzentop | Sep 28 | 4:15 PM | Mizzentop | - | Away | Cancelled |
| Varsity B Volleyball | vs. Miss Porter's School | Sep 29 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 2 - 3 | Home | |
| Boy's Varsity Soccer | vs. Avon Old Farms School | Sep 29 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 6 - 3 | Home | |
| Varsity Field Hockey | vs. Berkshire School | Sep 29 | 3:15 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 1 - 0 | Home | |
| Varsity Cross Country | @ Washington Montessori School (WMS) | Sep 29 | 3:45 PM | Washington Montessori School (WMS) | 15 - 40 | Away | |
| Varsity Football | vs. Brunswick School | Sep 29 | 4:00 PM | Roy Football Field - Football Field - 2800 | - | Home | Cancelled |
| Girl's Varsity Soccer | @ Foote School | Sep 29 | 4:00 PM | Foote School | 5 - 2 | Away | |
| Varsity Volleyball | @ Ethel Walker School | Oct 1 | 3:00 PM | Ethel Walker School | 0 - 2 | Away | |
| Varsity B Soccer | @ TBD | Oct 1 | 3:30 PM | Dutchess Day School | - | Away | |
| Junior Blue Soccer | @ TBD | Oct 1 | 3:30 PM | Dutchess Day School | - | Away | |
| Boy's Varsity Soccer | vs. Frederick Gunn School | Oct 1 | 4:00 PM | Seibert Memorial Field - Siebert Field - 2900 | 3 - 2 | Home | |
| Varsity Cross Country | vs. Indian Mountain School | Oct 1 | 4:00 PM | Playing Fields - Seibert Memorial Field | 24 - 34 | Home | |
| Girl's Varsity Soccer | @ Ethel Walker School | Oct 1 | 4:15 PM | Ethel Walker School | 3 - 0 | Away | |
| Girl's Varsity Soccer | @ TBD | Oct 1 | 4:15 PM | Hotchkiss School | - | Away | Rescheduled to Oct 1 |
| Girl's Varsity Soccer | @ Sherman Middle School | Oct 4 | 4:00 PM | Sherman Middle School | - | Away | Cancelled |
| Varsity Football | @ Taft School | Oct 4 | 4:00 PM | Taft School | 8 - 40 | Away | |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 5 | 4:00 PM | Dutchess Day School | 1 - 2 | Away | |
| Varsity Volleyball | vs. Kent School | Oct 6 | 3:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 1 - 3 | Home | |
| Girl's Varsity Soccer | vs. Canterbury School | Oct 6 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 7 - 1 | Home | |
| Boy's Varsity Soccer | @ Hotchkiss School | Oct 6 | 3:30 PM | Hotchkiss School | 0 - 3 | Away | |
| Varsity B Soccer | @ Sherman Middle School | Oct 6 | 3:30 PM | Sherman Middle School | 2 - 0 | Away | |
| Varsity B Volleyball | @ Oakwood Friends School | Oct 6 | 3:30 PM | Oakwood Friends School | 3 - 1 | Away | |
| Varsity Cross Country | vs. Kingswood-Oxford School | Oct 6 | 3:45 PM | Playing Fields - Seibert Memorial Field | 15 - 40 | Home | |
| Junior Blue Soccer | vs. Mizzentop | Oct 6 | 4:00 PM | Seibert Memorial Field - Siebert Field - 2900 | 2 - 4 | Home | |
| Varsity Field Hockey | @ Canterbury School | Oct 6 | 4:00 PM | Canterbury School | 3 - 1 | Away | |
| Varsity B Volleyball | vs. Indian Mountain School | Oct 8 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Junior Blue Soccer | @ Dutchess Day School | Oct 8 | 3:30 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Soccer | vs. Dutchess Day School | Oct 8 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Boy's Varsity Soccer | @ Millbrook School | Oct 8 | 4:00 PM | Millbrook School | 6 - 1 | Away | |
| Varsity Volleyball | @ Hopkins School | Oct 8 | 4:00 PM | Hopkins School | 3 - 1 | Away | |
| Varsity Field Hockey | @ Loomis Chaffee | Oct 8 | 4:30 PM | Loomis Chaffee | 7 - 0 | Away | |
| Girl's Varsity Soccer | vs. Miss Porter's School | Oct 9 | 2:30 PM | Seibert Memorial Field - Siebert Field - 2900 | 5 - 0 | Home | |
| Varsity Volleyball | @ TBD | Oct 11 | 4:00 PM | Kent School | - | Away | Rescheduled to Oct 14 |
| Junior Football | @ Greenwich Country Day | Oct 12 | 3:30 PM | Greenwich Country Day - Football Game | - | Away | Cancelled |
| Varsity B Field Hockey | vs. Mizzentop | Oct 12 | 4:00 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 0 - 0 | Home | |
| Varsity Volleyball | @ Kent School | Oct 12 | 4:00 PM | Kent School | 3 - 1 | Away | |
| Girl's Varsity Soccer | @ Sherman Middle School | Oct 12 | 4:00 PM | Sherman Middle School | 5 - 1 | Away | |
| Varsity B Soccer | @ Mizzentop | Oct 12 | 4:15 PM | Mizzentop | - | Away | Cancelled |
| Boy's Varsity Soccer | vs. Kent School | Oct 13 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 6 - 3 | Home | |
| Varsity Volleyball | @ Hotchkiss School | Oct 13 | 3:15 PM | Hotchkiss School | 3 - 0 | Away | |
| Varsity B Volleyball | vs. Forman School | Oct 13 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 1 | Home | |
| Varsity Field Hockey | vs. Hotchkiss School | Oct 13 | 3:15 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 5 - 0 | Home | |
| Junior Blue Soccer | @ Indian Mountain School | Oct 13 | 3:30 PM | Indian Mountain School | 1 - 2 | Away | |
| Varsity Cross Country | @ Millbrook School | Oct 13 | 3:30 PM | Millbrook School | - | Away | |
| Girl's Varsity Soccer | @ Miss Porter's School | Oct 13 | 4:30 PM | Miss Porter's School | 4 - 0 | Away | |
| Varsity B Soccer | @ Washington Montessori School (WMS) | Oct 14 | 3:45 PM | Washington Montessori School (WMS) | 8 - 2 | Away | |
| Varsity B Field Hockey | vs. Dutchess Day School | Oct 14 | 3:45 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 0 - 2 | Home | |
| Junior Blue Soccer | vs. Washington Montessori School (WMS) | Oct 14 | 3:45 PM | Playing Fields - Seibert Memorial Field | 5 - 2 | Home | |
| Girl's Varsity Soccer | vs. Washington Montessori School (WMS) | Oct 14 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 5 - 2 | Home | Cancelled |
| Varsity Volleyball | @ TBD | Oct 14 | 4:00 PM | Kent School | - | Away | Rescheduled to Oct 12 |
| Boy's Varsity Soccer | vs. Indian Mountain School | Oct 15 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 3 - 7 | Home | |
| Varsity Football | vs. Loomis Chaffee | Oct 15 | 4:15 PM | Roy Football Field - Football Field - 2800 | - | Home | Cancelled |
| Varsity Football | vs. TBD | Oct 15 | 4:30 PM | Roy Football Field - Football Field - 2800 | - | Home | |
| Varsity Football | vs. TBD | Oct 16 | 2:30 PM | Roy Football Field - Football Field - 2800 | - | Home | Rescheduled to Oct 15 |
| Varsity Volleyball | vs. Taft School | Oct 16 | 2:30 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Girl's Varsity Soccer | vs. Westminster School | Oct 16 | 2:30 PM | Seibert Memorial Field - Siebert Field - 2900 | 8 - 0 | Home | |
| Varsity Field Hockey | vs. Canterbury School | Oct 16 | 2:30 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 2 - 0 | Home | |
| Varsity B Soccer | vs. Trinity Pawling School | Oct 19 | 3:30 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Junior Blue Soccer | @ Mizzentop | Oct 19 | 4:15 PM | Mizzentop | 5 - 8 | Away | |
| Varsity B Volleyball | vs. Hopkins School | Oct 20 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Varsity B Soccer | @ Indian Mountain School | Oct 20 | 3:30 PM | Indian Mountain School | 2 - 2 | Away | |
| Junior Blue Soccer | vs. Renbrook School | Oct 21 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 2 - 4 | Home | |
| Varsity Cross Country | @ Indian Mountain School | Oct 22 | 4:00 PM | Indian Mountain School | - | Away | Cancelled |
| Girl's Varsity Soccer | @ Canterbury School | Oct 23 | 1:30 PM | Canterbury School | 8 - 1 | Away | |
| Varsity Volleyball | @ Choate Rosemary Hall | Oct 23 | 2:30 PM | Choate Rosemary Hall | 1 - 3 | Away | |
| Varsity Field Hockey | vs. Miss Porter's School | Oct 23 | 2:30 PM | Miss Porter's School | 3 - 0 | Home | |
| Varsity Football | @ TBD | Oct 26 | 3:30 PM | NCCS (New Canaan Country School) | - | Away | Rescheduled to Oct 28 |
| Junior Blue Soccer | @ TBD | Oct 26 | 4:00 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Field Hockey | @ Dutchess Day School | Oct 26 | 4:00 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Volleyball | vs. Hotchkiss School | Oct 27 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | 0 - 3 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Oct 27 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 2 - 4 | Home | |
| Varsity Volleyball | vs. Westover School | Oct 27 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 1 - 3 | Home | |
| Varsity B Soccer | @ Trinity Pawling School | Oct 27 | 3:30 PM | Trinity Pawling School | - | Away | Cancelled |
| Boy's Varsity Soccer | @ Choate Rosemary Hall | Oct 27 | 3:30 PM | Choate Rosemary Hall | 6 - 0 | Away | |
| Girl's Varsity Soccer | @ Berkshire School | Oct 27 | 3:30 PM | Berkshire School | - | Away | Cancelled |
| Varsity B Soccer | vs. Dutchess Day School | Oct 27 | 3:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 5 - 4 | Home | |
| Varsity Cross Country | @ Indian Mountain School | Oct 27 | 3:45 PM | Indian Mountain School | 19 - 36 | Away | |
| Varsity B Field Hockey | vs. Renbrook School | Oct 27 | 3:45 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 1 - 0 | Home | |
| Varsity Field Hockey | vs. Renbrook School | Oct 27 | 3:45 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | - | Home | Cancelled |
| Junior Football | @ NCCS (New Canaan Country School) | Oct 28 | 3:30 PM | NCCS (New Canaan Country School) | - | Away | |
| Varsity Football | @ NCCS (New Canaan Country School) | Oct 28 | 3:30 PM | NCCS (New Canaan Country School) | 20 - 16 | Away | |
| Junior Blue Soccer | @ Washington Montessori School (WMS) | Oct 28 | 3:45 PM | Washington Montessori School (WMS) | 5 - 6 | Away | |
| Girl's Varsity Soccer | @ Washington Montessori School (WMS) | Oct 28 | 3:45 PM | Washington Montessori School (WMS) | - | Away | Cancelled |
| Boy's Varsity Soccer | @ Foote School | Oct 28 | 4:00 PM | Foote School | - | Away | Cancelled |
| Varsity B Soccer | @ Renbrook School | Oct 28 | 4:00 PM | Renbrook School | 2 - 0 | Away | |
| Varsity B Field Hockey | vs. Mizzentop | Oct 28 | 4:00 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | 0 - 2 | Home | |
| Girl's Varsity Soccer | vs. Indian Mountain School | Oct 29 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 2 - 2 | Home | |
| Varsity B Volleyball | @ Indian Mountain School | Oct 29 | 3:30 PM | Indian Mountain School | 3 - 1 | Away | |
| Varsity Field Hockey | @ Taft School | Oct 29 | 4:00 PM | Taft School | 1 - 0 | Away | |
| Varsity Field Hockey | vs. Loomis Chaffee | Oct 30 | 2:30 PM | Cornell Athletic Field - Cornell Athletic Field - 2500 | - | Home | Cancelled |
| Varsity Football | vs. Eaglebrook School | Oct 30 | 2:30 PM | Roy Football Field - Football Field - 2800 | 6 - 12 | Home | |
| Varsity B Soccer | vs. Washington Montessori School (WMS) | Nov 1 | 3:30 PM | Seibert Memorial Field - Siebert Field - 2900 | 6 - 4 | Home | |
| Boy's Varsity Soccer | @ Avon Old Farms School | Nov 1 | 4:15 PM | Avon Old Farms School | 5 - 1 | Away | |
| Junior Football | @ Greenwich Country Day | Nov 2 | 3:30 PM | Greenwich Country Day - Football Game | 0 - 20 | Away | |
| Varsity B Field Hockey | @ Mizzentop | Nov 2 | 4:00 PM | Mizzentop | 0 - 1 | Away | |
| Varsity Volleyball | vs. Choate Rosemary Hall | Nov 3 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 1 | Home | |
| Boy's Varsity Soccer | vs. Westminster School | Nov 3 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 4 - 1 | Home | |
| Girl's Varsity Soccer | vs. Hotchkiss School | Nov 3 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Varsity Field Hockey | @ Westminster School | Nov 3 | 3:15 PM | Westminster School | 6 - 0 | Away | |
| Varsity Cross Country | @ Kingswood-Oxford School | Nov 3 | 3:30 PM | Kingswood-Oxford School | - | Away | |
| Varsity B Soccer | @ Mizzentop | Nov 3 | 3:45 PM | Mizzentop | 5 - 8 | Away | |
| Varsity Volleyball | @ Taft School | Nov 4 | 3:45 PM | Taft School | 1 - 3 | Away | |
| Varsity B Soccer | vs. Sherman Middle School | Nov 5 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Girl's Varsity Soccer | vs. Sherman Middle School | Nov 5 | 3:15 PM | Seibert Memorial Field - Siebert Field - 2900 | 7 - 0 | Home | |
| Junior Blue Soccer | vs. Dutchess Day School | Nov 5 | 3:45 PM | Pavek Athletic Field - Pavek Athletic Field - 2700 | 6 - 1 | Home | |
| Varsity Field Hockey | @ Frederick Gunn School | Nov 5 | 3:45 PM | Frederick Gunn School | 0 - 0 | Away | |
| Varsity B Volleyball | @ Hopkins School | Nov 5 | 4:15 PM | Hopkins School | 3 - 1 | Away | |
| Boy's Varsity Soccer | @ TBD | Nov 6 | 9:00 AM | Eaglebrook School | - | Away | |
| Girl's Varsity Soccer | @ TBD | Nov 6 | 10:30 AM | Indian Mountain School | - | Away | |
| Varsity Volleyball | vs. TBD | Nov 6 | 2:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | - | Home | |
| Varsity Cross Country | vs. Washington Montessori School (WMS) | Nov 8 | 3:30 PM | Playing Fields - Seibert Memorial Field | - | Home | |
| Varsity Volleyball | @ TBD | Nov 8 | 3:45 PM | Taft School | - | Away | Rescheduled to Nov 4 |
| Varsity B Soccer | @ Dutchess Day School | Nov 9 | 3:30 PM | Dutchess Day School | 2 - 3 | Away | |
| Boy's Varsity Soccer | vs. Salisbury School | Nov 10 | 3:00 PM | Seibert Memorial Field - Siebert Field - 2900 | - | Home | Cancelled |
| Girl's Varsity Soccer | @ Westminster School | Nov 10 | 3:00 PM | Westminster School | 10 - 0 | Away | |
| Varsity B Volleyball | @ Forman School | Nov 10 | 3:15 PM | Forman School | 3 - 1 | Away | |
| Varsity B Field Hockey | @ Renbrook School | Nov 10 | 3:15 PM | Renbrook School | 0 - 0 | Away | |
| Varsity Field Hockey | @ Hotchkiss School | Nov 10 | 3:15 PM | Hotchkiss School | 3 - 0 | Away | |
| Varsity Volleyball | vs. Kingswood-Oxford School | Nov 10 | 3:30 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Girl's Varsity Soccer | @ Indian Mountain School | Nov 11 | 3:30 PM | Indian Mountain School | 1 - 2 | Away | |
| Boy's Varsity Soccer | @ Indian Mountain School | Nov 11 | 6:30 PM | Hotchkiss School | 2 - 8 | Away | |
| Varsity Field Hockey | @ TBD | Nov 12 | 2:00 PM | Indian Mountain School | - | Away | |
| Varsity B Soccer | vs. Indian Mountain School | Nov 12 | 2:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 8 - 5 | Home | |
| Junior Blue Soccer | vs. Indian Mountain School | Nov 12 | 2:45 PM | Seibert Memorial Field - Siebert Field - 2900 | 4 - 7 | Home | |
| Varsity Cross Country | vs. Indian Mountain School | Nov 12 | 2:45 PM | Playing Fields - Seibert Memorial Field | - | Home | Cancelled |
| Varsity Volleyball | @ Indian Mountain School | Nov 12 | 3:00 PM | Indian Mountain School | 1 - 3 | Away | |
| Girl's Varsity Soccer | @ TBD | Nov 12 | 3:00 PM | Indian Mountain School | - | Away | Rescheduled to Nov 11 |
| Varsity B Volleyball | vs. Indian Mountain School | Nov 12 | 3:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Boy's Varsity Ice Hockey | @ Rectory School | Dec 4 | 2:30 PM | Rectory School | 0 - 2 | Away | |
| Boy's Varsity Ice Hockey | vs. Westminster School | Dec 8 | 3:15 PM | Lufkin Rink - Rink - 2600 | 3 - 3 | Home | |
| Boy's Varsity Ice Hockey | vs. Avon Old Farms School | Dec 11 | 2:30 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | @ NCCS (New Canaan Country School) | Jan 8 | 10:45 AM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Upland Country Day School | Jan 8 | 2:00 PM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Junior Flyers - 08s | Jan 9 | 8:00 AM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 9 | 12:00 PM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 9 | 1:15 PM | Upland Country Day School | - | Away | Cancelled |
| Varsity Ski Team | @ Indian Mountain School | Jan 10 | 3:30 PM | Mohawk Mountain Ski Area | 14 - 11 | Away | |
| Boy's Varsity B Basketball | vs. Dutchess Day School | Jan 11 | 3:45 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 12 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Kingswood-Oxford School | Jan 12 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | 20 - 27 | Home | |
| Girl's Varsity Ice Hockey | vs. Kent School | Jan 12 | 3:15 PM | Lufkin Rink - Rink - 2600 | 5 - 1 | Home | |
| Boy's Varsity Ice Hockey | @ Trinity Pawling School | Jan 12 | 3:30 PM | Trinity Pawling School | - | Away | Cancelled |
| Girl's Varsity Basketball | @ Sherman Middle School | Jan 13 | 3:30 PM | Sherman Middle School | 19 - 23 | Away | |
| Girl's Varsity B Basketball | @ Renbrook School | Jan 13 | 3:30 PM | Renbrook School | - | Away | Cancelled |
| Boy's Varsity B Basketball | vs. Sherman Middle School | Jan 13 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 28 - 33 | Home | |
| Boy's Varsity Basketball | @ Brunswick School | Jan 13 | 4:00 PM | Brunswick School | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Jan 14 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Jan 14 | 3:15 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Varsity B Ice Hockey | @ Eaglebrook School | Jan 14 | 4:00 PM | Eaglebrook School | 9 - 4 | Away | |
| Varsity B Ice Hockey | vs. Springfield Aces | Jan 15 | 11:00 AM | Lufkin Rink - Rink - 2600 | 1 - 14 | Home | |
| Boy's Varsity Ice Hockey | vs. Rhode Island Hitmen Hockey Club | Jan 15 | 1:30 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Boy's Varsity Basketball | @ TBD | Jan 16 | 8:00 AM | Suffield Academy | - | Away | Rescheduled to Feb 27 |
| Boy's Varsity B Basketball | vs. Trinity Pawling School | Jan 18 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Boy's Varsity Basketball | @ Canterbury School | Jan 19 | 2:30 PM | Canterbury School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | vs. Kent School | Jan 19 | 2:30 PM | Lufkin Rink - Rink - 2600 | 6 - 3 | Home | |
| Girl's Varsity Basketball | vs. Indian Mountain School | Jan 19 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Jan 19 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Jan 19 | 4:15 PM | Lufkin Rink - Rink - 2600 | 2 - 1 | Home | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Jan 20 | 3:30 PM | Washington Montessori School (WMS) | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Jan 20 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Winter Volleyball | vs. Dutchess Day School | Jan 20 | 3:45 PM | Athletics Building - Magnoli Gymnasium - Magnoli | - | Home | Cancelled |
| Boy's Varsity B Basketball | @ Kent Center School | Jan 20 | 4:00 PM | Kent Center School | - | Away | Cancelled |
| Girl's Varsity Basketball | @ Kent Center School | Jan 20 | 5:30 PM | Kent Center School | - | Away | Cancelled |
| Varsity Ski Team | @ Indian Mountain School | Jan 21 | 3:30 PM | Catamount Ski Area | - | Away | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Jan 21 | 4:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 56 - 19 | Home | |
| Varsity B Ice Hockey | vs. Eaglebrook School | Jan 21 | 4:30 PM | Lufkin Rink - Rink - 2600 | 3 - 1 | Home | |
| Girl's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 22 | 8:00 AM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 22 | 4:30 PM | Cardigan Mountain School | - | Away | Cancelled |
| Girl's Varsity Ice Hockey | @ Upland Country Day Ice Hockey Tournament | Jan 23 | 8:00 AM | Upland Country Day School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | @ Cardigan Mountain School | Jan 23 | 9:00 AM | Cardigan Mountain School | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | vs. Mizzentop | Jan 24 | 4:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 33 - 17 | Home | |
| Boy's Varsity B Basketball | @ Masters School (CT) | Jan 25 | 3:30 PM | The Masters School (CT) | 50 - 18 | Away | |
| Girl's Varsity B Basketball | @ Ethel Walker School | Jan 25 | 4:00 PM | Ethel Walker School | 12 - 40 | Away | |
| Girl's Varsity Ice Hockey | vs. Canterbury School | Jan 26 | 2:30 PM | Lufkin Rink - Rink - 2600 | 10 - 3 | Home | |
| Varsity Ski Team | @ Housatonic Regional High School | Jan 26 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Varsity Basketball | vs. Avon Old Farms School | Jan 26 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | 48 - 38 | Home | |
| Girl's Varsity Basketball | @ Canterbury School | Jan 26 | 4:00 PM | Canterbury School | 26 - 13 | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Jan 26 | 4:15 PM | Lufkin Rink - Rink - 2600 | 8 - 7 | Home | |
| Boy's Varsity Ice Hockey | @ Berkshire School | Jan 26 | 4:30 PM | Berkshire School | 8 - 4 | Away | |
| Girl's Varsity B Basketball | vs. Washington Montessori School (WMS) | Jan 27 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 20 - 32 | Home | |
| Boy's Varsity B Basketball | @ Sherman Middle School | Jan 27 | 3:30 PM | Sherman Middle School | - | Away | Cancelled |
| Boy's Jr. Blue Basketball | vs. Renbrook School | Jan 27 | 3:45 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 7 - 31 | Home | |
| Winter Volleyball | @ Dutchess Day School | Jan 27 | 3:45 PM | Dutchess Day School | 1 - 3 | Away | |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Jan 28 | 2:15 PM | Hotchkiss School | 3 - 5 | Away | |
| Girl's Varsity Basketball | @ Indian Mountain School | Jan 28 | 2:45 PM | Indian Mountain School | 31 - 17 | Away | |
| Varsity Ski Team | @ Indian Mountain School | Jan 28 | 3:30 PM | Catamount Ski Area | - | Away | |
| Boy's Varsity Basketball | @ Indian Mountain School | Jan 28 | 4:15 PM | Indian Mountain School | 39 - 71 | Away | |
| Varsity B Ice Hockey | vs. Springfield Aces | Jan 28 | 7:00 PM | Lufkin Rink - Rink - 2600 | 3 - 4 | Home | |
| Boy's Varsity Ice Hockey | vs. Upland Country Day School | Jan 29 | 8:30 AM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | vs. Upland Country Day School | Jan 29 | 10:30 AM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Girls Varsity B Ice Hockey | vs. Danbury Hat Tricks U14 Girls | Jan 29 | 12:15 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Boy's Varsity Basketball | vs. Hotchkiss School | Jan 29 | 2:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | @ Kent School | Jan 29 | 4:30 PM | Kent School | - | Away | Cancelled |
| Girl's Varsity B Basketball | vs. Washington Montessori School (WMS) | Jan 31 | 3:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 14 - 17 | Home | |
| Boy's Varsity Basketball | @ Trinity Pawling School | Jan 31 | 3:45 PM | Trinity Pawling School | 41 - 46 | Away | |
| Boy's Varsity Ice Hockey | vs. Brunswick School | Jan 31 | 3:45 PM | Lufkin Rink - Rink - 2600 | 7 - 8 | Home | |
| Boy's Varsity B Basketball | vs. Mizzentop | Jan 31 | 4:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 45 - 27 | Home | |
| Boy's Jr. Blue Basketball | vs. Washington Montessori School (WMS) | Jan 31 | 4:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 20 - 23 | Home | |
| Boy's Jr. Blue Basketball | @ Sherman Middle School | Feb 1 | 3:30 PM | Sherman Middle School | 14 - 14 | Away | |
| Girl's Varsity Basketball | @ Foote School | Feb 1 | 3:30 PM | Foote School | 31 - 12 | Away | |
| Girl's Varsity Basketball | vs. Hotchkiss School | Feb 2 | 3:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 47 - 13 | Home | |
| Boy's Varsity Ice Hockey | vs. Taft School | Feb 2 | 3:15 PM | Lufkin Rink - Rink - 2600 | 5 - 4 | Home | |
| Boy's Varsity B Basketball | vs. Hopkins School | Feb 2 | 3:30 PM | Playing Fields - Blue Dog Gymnasium | 22 - 51 | Home | |
| Boy's Varsity Basketball | vs. Hopkins School | Feb 2 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 2 | 4:00 PM | Mohawk Mountain Ski Area | - | Away | |
| Girls Varsity B Ice Hockey | @ Millbrook School | Feb 2 | 4:00 PM | Millbrook School | 3 - 4 | Away | |
| Girl's Varsity Ice Hockey | @ Millbrook School | Feb 2 | 4:00 PM | Millbrook School | - | Away | Cancelled |
| Winter Volleyball | vs. Dutchess Day School | Feb 3 | 3:45 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 1 - 2 | Home | |
| Girl's Varsity B Basketball | vs. Renbrook School | Feb 3 | 3:45 PM | Athletics Building - Blue Dog Gym - BD Gym | 26 - 15 | Home | |
| Girl's Varsity Ice Hockey | @ Taft School | Feb 3 | 4:15 PM | Taft School | 2 - 0 | Away | |
| Varsity B Ice Hockey | @ Indian Mountain School | Feb 4 | 3:00 PM | Hotchkiss School | - | Away | Cancelled |
| Boy's Varsity Ice Hockey | vs. Indian Mountain School | Feb 4 | 3:15 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Boy's Jr. Blue Basketball | vs. Indian Mountain School | Feb 4 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | - | Home | Cancelled |
| Boy's Varsity B Basketball | vs. Indian Mountain School | Feb 4 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Girl's Varsity Basketball | @ Masters School (CT) | Feb 4 | 3:30 PM | The Masters School (CT) | - | Away | Cancelled |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 9 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Feb 9 | 3:15 PM | Indian Mountain School | 22 - 25 | Away | |
| Girl's Varsity Ice Hockey | vs. Hotchkiss School | Feb 9 | 3:15 PM | Lufkin Rink - Rink - 2600 | 7 - 0 | Home | |
| Boy's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 9 | 3:30 PM | Washington Montessori School (WMS) | 32 - 23 | Away | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Feb 10 | 3:30 PM | Washington Montessori School (WMS) | 26 - 16 | Away | |
| Girl's Varsity Basketball | vs. Sherman Middle School | Feb 10 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 46 - 21 | Home | |
| Girl's Varsity B Basketball | vs. Sherman Middle School | Feb 10 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Winter Volleyball | @ Dutchess Day School | Feb 10 | 3:45 PM | Dutchess Day School | 2 - 0 | Away | |
| Junior Red Basketball | vs. Mizzentop | Feb 10 | 4:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 15 - 40 | Home | |
| Boy's Varsity Basketball | vs. Salisbury School | Feb 11 | 3:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 34 - 30 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 11 | 3:00 PM | Lufkin Rink - Rink - 2600 | 7 - 2 | Home | |
| Girl's Varsity Ice Hockey | @ Berkshire School | Feb 11 | 3:30 PM | Berkshire School | 7 - 2 | Away | |
| Varsity Ski Team | @ Indian Mountain School | Feb 11 | 3:30 PM | Catamount Ski Area | - | Away | |
| Girl's Varsity B Basketball | @ Hotchkiss School | Feb 11 | 4:30 PM | Hotchkiss School | 8 - 20 | Away | |
| Boy's Varsity B Basketball | @ Maplebrook School Boys Basketball Tournament | Feb 12 | 10:00 AM | Maplebrook School | - | Away | Cancelled |
| Boy's Varsity Basketball | vs. Indian Mountain School | Feb 12 | 1:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 28 - 59 | Home | |
| Girl's Varsity Ice Hockey | @ Westminster School | Feb 12 | 1:00 PM | Westminster School | 6 - 3 | Away | |
| Boy's Varsity Ice Hockey | vs. Kent School | Feb 12 | 2:30 PM | Lufkin Rink - Rink - 2600 | 2 - 1 | Home | |
| Girl's Varsity Basketball | vs. Canterbury School | Feb 12 | 2:30 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 35 - 12 | Home | |
| Varsity Ski Team | @ Washington Montessori School (WMS) | Feb 14 | 3:30 PM | Mohawk Mountain Ski Area | - | Away | |
| Boy's Jr. Blue Basketball | vs. Sherman Middle School | Feb 14 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 24 - 6 | Home | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 14 | 3:30 PM | Washington Montessori School (WMS) | 7 - 29 | Away | |
| Boy's Varsity B Basketball | @ Trinity Pawling School | Feb 15 | 3:45 PM | Trinity Pawling School | 28 - 15 | Away | |
| Boy's Varsity Basketball | vs. Foote School | Feb 15 | 3:45 PM | Athletics Building - Blue Dog Gym - BD Gym | 64 - 47 | Home | |
| Girl's Varsity B Basketball | vs. Kent Center School | Feb 15 | 4:00 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 18 - 22 | Home | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 16 | 2:30 PM | Lufkin Rink - Rink - 2600 | 5 - 5 | Home | |
| Girl's Varsity Ice Hockey | @ Canterbury School | Feb 16 | 2:30 PM | Canterbury School | 9 - 2 | Away | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 16 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | |
| Girl's Varsity Basketball | vs. Ethel Walker School | Feb 16 | 3:15 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 34 - 19 | Home | |
| Boy's Varsity B Basketball | vs. Washington Montessori School (WMS) | Feb 16 | 3:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 34 - 15 | Home | |
| Boy's Jr. Blue Basketball | @ Washington Montessori School (WMS) | Feb 16 | 3:30 PM | Washington Montessori School (WMS) | 16 - 10 | Away | |
| Boy's Varsity Ice Hockey | vs. Brunswick School | Feb 16 | 4:00 PM | Lufkin Rink - Rink - 2600 | 3 - 6 | Home | |
| Girl's Varsity B Basketball | @ Washington Montessori School (WMS) | Feb 17 | 3:30 PM | Washington Montessori School (WMS) | 23 - 33 | Away | |
| Winter Volleyball | @ Dutchess Day School | Feb 17 | 3:45 PM | Dutchess Day School | 2 - 1 | Away | |
| Boy's Jr. Blue Basketball | @ Indian Mountain School | Feb 18 | 2:45 PM | Indian Mountain School | 25 - 28 | Away | |
| Boy's Varsity Basketball | vs. Frederick Gunn School | Feb 18 | 4:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 54 - 51 | Home | |
| Girl's Varsity Basketball | @ Frederick Gunn School | Feb 18 | 4:00 PM | Frederick Gunn School | 38 - 19 | Away | |
| Boy's Varsity B Basketball | @ Indian Mountain School | Feb 18 | 4:15 PM | Indian Mountain School | 27 - 25 | Away | |
| Boy's Varsity Ice Hockey | vs. Rectory School | Feb 18 | 5:00 PM | Lufkin Rink - Rink - 2600 | 1 - 3 | Home | |
| Girl's Varsity Ice Hockey | @ Taft School | Feb 18 | 6:30 PM | Taft School | 0 - 1 | Away | |
| Girl's Varsity Ice Hockey | vs. Przygocki Cup Girls Ice Hockey Tournament | Feb 19 | 11:30 AM | Lufkin Rink - Rink - 2600 | - | Home | |
| Girl's Varsity Ice Hockey | vs. Przygocki Cup Girls Ice Hockey Tournament | Feb 19 | 2:30 PM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Basketball | vs. Westminster School | Feb 19 | 2:30 PM | Athletics Building - Blue Dog Gym - BD Gym | 49 - 37 | Home | |
| Girl's Varsity Ice Hockey | vs. Przygocki Cup Girls Ice Hockey Tournament | Feb 19 | 4:45 PM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Basketball | vs. Canterbury School | Feb 21 | 4:15 PM | Athletics Building - Blue Dog Gym - BD Gym | 50 - 48 | Home | |
| Boy's Varsity Ice Hockey | @ Westminster School | Feb 21 | 4:30 PM | Westminster School | 2 - 5 | Away | |
| Junior Red Basketball | @ Dutchess Day School | Feb 22 | 3:45 PM | Dutchess Day School | 6 - 13 | Away | |
| Winter Volleyball | vs. Dutchess Day School | Feb 22 | 3:45 PM | Athletics Building - Magnoli Gymnasium - Magnoli | 3 - 0 | Home | |
| Boy's Varsity Ice Hockey | @ Salisbury School | Feb 23 | 3:00 PM | Salisbury School | 5 - 7 | Away | |
| Girl's Varsity Basketball | vs. Indian Mountain School | Feb 23 | 3:15 PM | Athletics Building - Blue Dog Gym - BD Gym | 13 - 26 | Home | |
| Varsity Ski Team | @ BHSL (Berkshire Hills Ski League) | Feb 23 | 3:15 PM | Mohawk Mountain Ski Area | - | Away | Cancelled |
| Girls Varsity B Ice Hockey | vs. Millbrook School | Feb 23 | 3:30 PM | Lufkin Rink - Rink - 2600 | 1 - 5 | Home | |
| Girl's Varsity Ice Hockey | vs. Millbrook School | Feb 23 | 3:30 PM | Lufkin Rink - Rink - 2600 | - | Home | Cancelled |
| Boy's Varsity Basketball | @ Berkshire School | Feb 23 | 4:30 PM | Berkshire School | 28 - 43 | Away | |
| Varsity B Ice Hockey | vs. Indian Mountain School | Feb 24 | 3:00 PM | Lufkin Rink - Rink - 2600 | 6 - 8 | Home | |
| Boy's Jr. Blue Basketball | @ Renbrook School | Feb 24 | 3:30 PM | Renbrook School | 18 - 35 | Away | |
| Boy's Varsity B Basketball | vs. Kent Center School | Feb 24 | 4:00 PM | Athletics Building - Blue Dog Gym - BD Gym | 38 - 14 | Home | |
| Boy's Varsity Basketball | @ Frederick Gunn School | Feb 24 | 4:30 PM | Frederick Gunn School | 47 - 38 | Away | |
| Girl's Varsity Ice Hockey | vs. Berkshire School | Feb 24 | 4:30 PM | Lufkin Rink - Rink - 2600 | 9 - 1 | Home | |
| Varsity B Ice Hockey | vs. TBD | Feb 25 | 2:30 PM | Lufkin Rink - Rink - 2600 | - | Home | Rescheduled to Feb 24 |
| Varsity Ski Team | @ Indian Mountain School | Feb 25 | 3:30 PM | Catamount Ski Area | - | Away | Cancelled |
| Boy's Varsity Basketball | @ TBD | Feb 25 | 4:00 PM | Frederick Gunn School | - | Away | Rescheduled to Feb 24 |
| Girl's Varsity Basketball | vs. Berkshire School | Feb 25 | 4:30 PM | Athletics Building - Blue Dog Gym - BD Gym | - | Home | Cancelled |
| Girl's Varsity Ice Hockey | vs. TBD | Feb 25 | 4:30 PM | Lufkin Rink - Rink - 2600 | - | Home | Rescheduled to Feb 24 |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 26 | 10:30 AM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 26 | 3:00 PM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Basketball | @ Suffield Academy Boys Basketball Tournament | Feb 27 | 9:30 AM | Suffield Academy | - | Away | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 27 | 11:00 AM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Ice Hockey | vs. Pavek Cup Boys Ice Hockey Tournament | Feb 27 | 2:00 PM | Lufkin Rink - Rink - 2600 | - | Home | |
| Boy's Varsity Ice Hockey | @ Indian Mountain School | Feb 28 | 7:15 PM | Silo Ridge | - | Away | |
| Boy's Varsity Lacrosse | @ Hamden Hall | Apr 12 | 4:00 PM | Hamden Hall | 11 - 1 | Away | |
| Varsity B Baseball | @ Kent Center School | Apr 12 | 4:00 PM | Kent Center School | - | Away | Cancelled |
| Varsity Softball | vs. Hopkins School | Apr 13 | 3:15 PM | Playing Fields - Seibert Memorial Field | 17 - 5 | Home | |
| Girl's Varsity Lacrosse | @ Westminster School | Apr 13 | 3:15 PM | Westminster School | 6 - 6 | Away | |
| Varsity Baseball | vs. Berkshire School | Apr 13 | 3:15 PM | Playing Fields - Seibert Memorial Field | 5 - 14 | Home | |
| Boy's Varsity Lacrosse | @ Trinity Pawling School | Apr 13 | 3:30 PM | Trinity Pawling School | 8 - 6 | Away | |
| Boy's Varsity B Lacrosse | vs. Dutchess Day School | Apr 13 | 3:45 PM | Playing Fields - Roy Football Field | 1 - 11 | Home | |
| Varsity A Tennis | @ Foote School | Apr 13 | 4:00 PM | Foote School | - | Away | Cancelled |
| Varsity Softball | @ Foote School | Apr 14 | 4:00 PM | Foote School | 5 - 4 | Away | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | Apr 15 | 2:30 PM | Playing Fields - Cornell Athletic Field | 4 - 4 | Home | |
| Varsity B Tennis | @ Indian Mountain School | Apr 15 | 3:15 PM | Indian Mountain School | 3 - 4 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | Apr 15 | 3:15 PM | Playing Fields - Roy Football Field | 1 - 4 | Home | |
| Varsity A Tennis | @ Millbrook School | Apr 15 | 4:00 PM | Millbrook School | 7 - 1 | Away | |
| Girl's Varsity Lacrosse | vs. Kent School | Apr 15 | 4:15 PM | Playing Fields - Cornell Athletic Field | 10 - 11 | Home | |
| Girl's Varsity Lacrosse | @ Millbrook School | Apr 18 | 4:00 PM | Millbrook School | 9 - 6 | Away | |
| Girl's Varsity B Lacrosse | vs. TBD | Apr 19 | 3:45 PM | Playing Fields - Cornell Athletic Field | - | Home | Rescheduled to Apr 21 |
| Varsity Softball | @ Hamden Hall | Apr 19 | 4:00 PM | Hamden Hall | 7 - 9 | Away | |
| Boy's Varsity B Lacrosse | @ Trinity Pawling School | Apr 19 | 4:00 PM | Trinity Pawling School | - | Away | Cancelled |
| Varsity A Tennis | vs. Taft School | Apr 20 | 2:30 PM | Athletics Building - Indoor Tennis - Tennis Cts | 7 - 2 | Home | |
| Girl's Varsity Lacrosse | vs. Berkshire School | Apr 20 | 3:15 PM | Playing Fields - Cornell Athletic Field | 10 - 7 | Home | |
| Varsity Baseball | @ Berkshire School | Apr 20 | 3:30 PM | Berkshire School | 12 - 15 | Away | |
| Boy's Varsity Lacrosse | @ Rectory School | Apr 20 | 4:00 PM | Avon Old Farms School | 11 - 2 | Away | |
| Varsity A Tennis | vs. Renbrook School | Apr 21 | 3:45 PM | Athletics Building - Indoor Tennis - Tennis Cts | 7 - 1 | Home | |
| Varsity Softball | vs. Renbrook School | Apr 21 | 3:45 PM | Playing Fields - Seibert Memorial Field | 1 - 8 | Home | |
| Girl's Varsity B Lacrosse | vs. Dutchess Day School | Apr 21 | 3:45 PM | Playing Fields - Cornell Athletic Field | - | Home | Cancelled |
| Girl's Varsity B Lacrosse | vs. Mizzentop | Apr 21 | 4:15 PM | Playing Fields - Cornell Athletic Field | 5 - 6 | Home | |
| Varsity B Tennis | vs. Indian Mountain School | Apr 22 | 2:45 PM | Athletics Building - Indoor Tennis - Tennis Cts | 9 - 0 | Home | |
| Varsity Baseball | vs. Trinity Pawling School | Apr 22 | 3:15 PM | Playing Fields - Seibert Memorial Field | 1 - 15 | Home | |
| Boy's Varsity Lacrosse | @ Taft School | Apr 22 | 3:45 PM | Taft School | 13 - 3 | Away | |
| Varsity A Tennis | @ Washington Montessori School (WMS) | Apr 25 | 3:45 PM | Washington Montessori School (WMS) | 8 - 1 | Away | |
| Varsity Baseball | @ Kingswood-Oxford School | Apr 25 | 4:15 PM | Kingswood-Oxford School | 1 - 12 | Away | |
| Varsity B Tennis | vs. Dutchess Day School | Apr 26 | 3:45 PM | Athletics Building - Indoor Tennis - Tennis Cts | 5 - 4 | Home | |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | Apr 26 | 4:00 PM | Indian Mountain School | 3 - 2 | Away | |
| Varsity A Tennis | vs. Hotchkiss School | Apr 27 | 2:30 PM | Athletics Building - Indoor Tennis - Tennis Cts | 5 - 4 | Home | |
| Varsity Softball | vs. Indian Mountain School | Apr 27 | 3:15 PM | Playing Fields - Seibert Memorial Field | 20 - 11 | Home | |
| Girl's Varsity Lacrosse | vs. Indian Mountain School | Apr 27 | 3:15 PM | Playing Fields - Cornell Athletic Field | 8 - 10 | Home | |
| Boy's Varsity B Lacrosse | @ TBD | Apr 27 | 3:15 PM | Indian Mountain School | - | Away | Rescheduled to Apr 26 |
| Boy's Varsity Lacrosse | vs. Hopkins School | Apr 27 | 3:30 PM | Hopkins School | 8 - 2 | Home | |
| Varsity B Baseball | @ Renbrook School | Apr 27 | 3:30 PM | Renbrook School | 4 - 3 | Away | |
| Varsity Crew | @ Salisbury School | Apr 27 | 3:30 PM | Salisbury School | - | Away | |
| Varsity Softball | @ Sherman Middle School | Apr 28 | 3:45 PM | Home | 3 - 8 | Away | |
| Girl's Varsity B Lacrosse | vs. Mizzentop | Apr 28 | 4:00 PM | Playing Fields - Cornell Athletic Field | 4 - 8 | Home | |
| Varsity B Tennis | @ Indian Mountain School | Apr 29 | 3:00 PM | Indian Mountain School | 4 - 5 | Away | |
| Varsity Baseball | @ Indian Mountain School | Apr 29 | 3:15 PM | Indian Mountain School | 2 - 18 | Away | |
| Girl's Varsity Lacrosse | @ Loomis Chaffee | Apr 29 | 4:00 PM | Loomis Chaffee | 6 - 0 | Away | |
| Varsity A Tennis | @ Berkshire School | Apr 29 | 4:00 PM | Berkshire School | 2 - 8 | Away | |
| Varsity Crew | vs. Westover School | Apr 29 | 4:00 PM | Lake Waramaug - RHS Crew Home | - | Home | Cancelled |
| Varsity A Tennis | vs. Indian Mountain School | May 2 | 3:45 PM | Athletics Building - Indoor Tennis - Tennis Cts | 5 - 4 | Home | |
| Varsity Baseball | vs. Canterbury School | May 2 | 4:30 PM | Playing Fields - Seibert Memorial Field | - | Home | Cancelled |
| Girl's Varsity Lacrosse | @ Indian Mountain School | May 3 | 4:00 PM | Indian Mountain School | 8 - 11 | Away | |
| Varsity Softball | @ Renbrook School | May 3 | 4:00 PM | Renbrook School | 12 - 2 | Away | |
| Varsity B Tennis | @ Westminster School | May 3 | 4:30 PM | Westminster School | 7 - 0 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | May 4 | 3:15 PM | Roy Football Field - Football Field - 2800 | 3 - 3 | Home | |
| Boy's Varsity Lacrosse | @ Salisbury School | May 4 | 3:15 PM | Salisbury School | 5 - 14 | Away | |
| Varsity A Tennis | vs. Hamden Hall | May 4 | 3:30 PM | Athletics Building - Indoor Tennis - Tennis Cts | 9 - 0 | Home | |
| Varsity Crew | @ Hotchkiss School | May 4 | 3:30 PM | Hotchkiss School | - | Away | |
| Varsity B Baseball | vs. Berkshire Waldorf School | May 4 | 3:45 PM | Playing Fields - Pavek Athletic Field | - | Home | Cancelled |
| Varsity Baseball | @ Brunswick School | May 4 | 3:45 PM | Brunswick School | - | Away | Cancelled |
| Girl's Varsity B Lacrosse | vs. Litchfield Hills Youth Lacrosse | May 4 | 4:30 PM | Playing Fields - Cornell Athletic Field | 8 - 9 | Home | |
| Boy's Varsity B Lacrosse | vs. Trinity Pawling School | May 5 | 3:30 PM | Playing Fields - Roy Football Field | - | Home | Cancelled |
| Varsity B Tennis | vs. Indian Mountain School | May 6 | 3:00 PM | Athletics Building - Indoor Tennis - Tennis Cts | - | Home | Cancelled |
| Girl's Varsity B Lacrosse | @ Indian Mountain School | May 6 | 3:15 PM | Indian Mountain School | 7 - 11 | Away | |
| Varsity B Baseball | @ Indian Mountain School | May 6 | 3:15 PM | Salisbury Town Field | 5 - 6 | Away | |
| Girl's Varsity Lacrosse | vs. Hotchkiss School | May 6 | 4:30 PM | Playing Fields - Cornell Athletic Field | 4 - 8 | Home | |
| Varsity Softball | vs. Westover School | May 7 | 2:30 PM | Playing Fields - Seibert Memorial Field | 17 - 4 | Home | |
| Varsity A Tennis | vs. Trinity Pawling School | May 7 | 2:30 PM | Athletics Building - Indoor Tennis - Tennis Cts | 9 - 0 | Home | |
| Boy's Varsity Lacrosse | vs. Indian Mountain School | May 7 | 2:30 PM | Playing Fields - Roy Football Field | 2 - 6 | Home | |
| Girl's Varsity Lacrosse | vs. Westminster School | May 7 | 2:30 PM | Playing Fields - Cornell Athletic Field | - | Home | Cancelled |
| Varsity Crew | @ TBD | May 8 | 7:30 AM | Lake Waramaug - RHS Crew Home | - | Away | Cancelled |
| Girl's Varsity B Lacrosse | @ Dutchess Day School | May 10 | 3:45 PM | Dutchess Day School | - | Away | Cancelled |
| Varsity B Tennis | vs. Westminster School | May 11 | 2:45 PM | Athletics Building - Indoor Tennis - Tennis Cts | 0 - 9 | Home | |
| Varsity B Baseball | vs. Indian Mountain School | May 11 | 3:00 PM | Playing Fields - Pavek Athletic Field | 3 - 4 | Home | |
| Girl's Varsity Lacrosse | vs. Ethel Walker School | May 11 | 3:00 PM | Playing Fields - Cornell Athletic Field | 7 - 5 | Home | |
| Boy's Varsity Lacrosse | vs. Salisbury School | May 11 | 3:00 PM | Playing Fields - Roy Football Field | - | Home | Cancelled |
| Varsity Crew | @ Berkshire School | May 11 | 3:30 PM | Berkshire School | - | Away | |
| Varsity Baseball | vs. Foote School | May 11 | 4:00 PM | Playing Fields - Seibert Memorial Field | - | Home | Cancelled |
| Boy's Varsity B Lacrosse | vs. Trinity Pawling School | May 12 | 3:30 PM | Playing Fields - Roy Football Field | - | Home | Cancelled |
| Boy's Varsity B Lacrosse | @ Indian Mountain School | May 13 | 3:30 PM | Indian Mountain School | 5 - 7 | Away | |
| Varsity A Tennis | vs. Frederick Gunn School | May 13 | 3:45 PM | Eren Family Tennis Center - Eren Family Tennis Center - 3000 | 7 - 2 | Home | |
| Varsity Baseball | vs. Frederick Gunn School | May 13 | 3:45 PM | Playing Fields - Seibert Memorial Field | - | Home | Cancelled |
| Boy's Varsity Lacrosse | vs. Taft School | May 13 | 4:00 PM | Playing Fields - Roy Football Field | - | Home | Cancelled |
| Varsity B Tennis | @ Indian Mountain School | May 13 | 4:00 PM | Indian Mountain School | 9 - 1 | Away | |
| Varsity Softball | @ Westover School | May 13 | 4:00 PM | Westover School | - | Away | Cancelled |
| Girl's Varsity B Lacrosse | @ Mizzentop | May 13 | 4:00 PM | Mizzentop | 13 - 18 | Away | |
| Girl's Varsity Lacrosse | vs. TBD | May 14 | 9:00 AM | Cornell Athletic Field - Cornell Athletic Field - 2500 | - | Home | |
| Varsity Crew | @ Litchfield Hills Rowing Club | May 14 | 10:00 AM | Litchfield Hills Rowing Club - Boathouse | - | Away | |
| Varsity B Tennis | vs. Washington Montessori School (WMS) | May 16 | 3:15 PM | Athletics Building - Indoor Tennis - Tennis Cts | 7 - 2 | Home | |
| Varsity Softball | vs. Sherman Middle School | May 16 | 3:45 PM | Playing Fields - Seibert Memorial Field | - | Home | Cancelled |
| Varsity B Baseball | vs. Renbrook School | May 17 | 3:45 PM | Playing Fields - Pavek Athletic Field | 7 - 1 | Home | |
| Boy's Varsity B Lacrosse | @ Dutchess Day School | May 17 | 3:45 PM | Dutchess Day School | 3 - 12 | Away | |
| Girl's Varsity B Lacrosse | @ TBD | May 17 | 4:00 PM | Mizzentop | - | Away | Rescheduled to May 13 |
| Varsity Crew | @ Lower Boat Regatta | May 18 | 3:00 PM | Lake Waramaug - RHS Crew Home | - | Away | |
| Varsity Softball | @ Indian Mountain School | May 18 | 3:15 PM | Indian Mountain School | 11 - 3 | Away | |
| Varsity A Tennis | @ Kent School | May 18 | 3:15 PM | Kent School | 5 - 4 | Away | |
| Girl's Varsity Lacrosse | vs. Canterbury School | May 18 | 3:15 PM | Playing Fields - Cornell Athletic Field | 9 - 14 | Home | |
| Varsity Baseball | vs. Hamden Hall | May 18 | 3:30 PM | Playing Fields - Seibert Memorial Field | 0 - 13 | Home | |
| Boy's Varsity Lacrosse | @ Hopkins School | May 18 | 3:30 PM | Hopkins School | 9 - 1 | Away | |
| Varsity B Tennis | vs. Mizzentop | May 19 | 4:00 PM | Eren Family Tennis Center - Eren Family Tennis Center - 3000 | 9 - 0 | Home | |
| Girl's Varsity B Lacrosse | vs. Litchfield Hills Youth Lacrosse | May 19 | 4:30 PM | Playing Fields - Cornell Athletic Field | - | Home | Cancelled |
| Varsity B Tennis | vs. Kent Center School | May 23 | 3:45 PM | Eren Family Tennis Center - Eren Family Tennis Center - 3000 | 7 - 0 | Home | |
| Varsity A Tennis | @ Indian Mountain School | May 23 | 4:00 PM | Indian Mountain School | 5 - 4 | Away | |
| Varsity B Baseball | vs. Kent Center School | May 23 | 4:00 PM | Playing Fields - Pavek Athletic Field | 4 - 0 | Home | |
| Boy's Varsity Lacrosse | @ Indian Mountain School | May 23 | 4:00 PM | Indian Mountain School | 3 - 10 | Away | |
| Girl's Varsity Lacrosse | @ Taft School | May 23 | 4:00 PM | Taft School | 10 - 3 | Away | |
| Varsity Softball | vs. Sherman Middle School | May 24 | 3:45 PM | Home | 0 - 3 | Home | |
| Varsity B Tennis | @ Dutchess Day School | May 24 | 4:00 PM | Dutchess Day School | 6 - 3 | Away | |
| Varsity Baseball | @ Avon Old Farms School | May 24 | 4:00 PM | Avon Old Farms School | 5 - 6 | Away | |
| Boy's Varsity B Lacrosse | vs. Indian Mountain School | May 24 | 4:00 PM | Playing Fields - Roy Football Field | 1 - 4 | Home | |
| Boy's Varsity Lacrosse | vs. Kent School | May 25 | 3:15 PM | Playing Fields - Roy Football Field | 10 - 5 | Home | |
| Varsity Baseball | vs. Indian Mountain School | May 25 | 3:15 PM | Indian Mountain School | 0 - 14 | Home | |
| Varsity Softball | vs. Indian Mountain School | May 25 | 3:15 PM | Playing Fields - Seibert Memorial Field | 9 - 2 | Home | |
| Girl's Varsity B Lacrosse | vs. Indian Mountain School | May 25 | 3:15 PM | Playing Fields - Cornell Athletic Field | 4 - 5 | Home | |
| Varsity B Baseball | @ Berkshire Waldorf School | May 25 | 3:30 PM | Berkshire Waldorf School | 9 - 16 | Away | |
| Varsity A Tennis | vs. Salisbury School | May 25 | 3:30 PM | Eren Family Tennis Center - Eren Family Tennis Center - 3000 | 9 - 0 | Home | |
| Girl's Varsity Lacrosse | @ Rectory School | May 25 | 4:00 PM | Ethel Walker School | 11 - 6 | Away | |
| No events found. | |||||||
