December 11, 2025
| Date | Opponent | Time | |
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| Wed | Nov 19 | vs. South Kent(S) | 4:00 PM |
| Mon | Dec 1 | Frederick Gunn School(S) (note) | 10:00 AM |
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Piatelli Jamboree at Berkshire School
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| Mon | Dec 1 | Dexter(S) (note) | 1:30 PM |
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Piatelli Jamboree at Berkshire School
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| Wed | Dec 3 | 3:00 PM | |
| Sat | Dec 6 | vs. Hotchkiss | 3:30 PM |
| Wed | Dec 10 | vs. Berkshire | 2:30 PM |
| Sat | Dec | vs. Loomis Chaffee | X:45 PM |
| Wed | Dec | vs. Salisbury | X:30 PM |
| Fri | Dec | Worcester Academy | X:00 PM |
| Fri | Dec 19- Dec 20 | William Barber Memorial Tournament | |
| Fri | Jan | @ Cushing | X:15 PM |
| Fri | Jan 2- Jan 4 | E.G. Watkins-Cushing Academy New Years Tournament | |
| Wed | Jan | @ Williston Northampton | X:30 PM |
| Sat | Jan | vs. Lawrence Academy | X:00 PM |
| Wed | Jan | vs. Choate | X:45 PM |
| Fri | Jan | @ Frederick Gunn School | X:00 PM |
| Wed | Jan | vs. Westminster | X:30 PM |
| Sat | Jan | @ Taft | X:15 PM |
| Mon | Jan | vs. Millbrook | X:15 PM |
| Wed | Jan | vs. Albany Academy | X:30 PM |
| Sat | Jan | @ Pomfret | X:15 PM |
| Sun | Feb | @ Winchendon | X:00 PM |
| Wed | Feb | @ Berkshire | X:00 PM |
| Wed | Feb | vs. Trinity-Pawling | X:00 PM |
| Sat | Feb | @ Cushing | X:00 PM |
| Mon | Feb | vs. Frederick Gunn School | X:00 PM |
| Wed | Feb | vs. Williston Northampton | X:00 PM |
| Sat | Feb | @ Kent | X:00 PM |
| Wed | Feb | @ Avon Old Farms | X:30 PM |
| Sat | Feb | vs. Wilbraham & Monson | X:30 PM |
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