| Date | Opponent | Time | |
| Fri | Nov | @ Trinity-Pawling (S) | X:45 PM |
| Sun | Nov 25 - Nov 26 | St. Paul's Jamboree (note) | |
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@ St. Paul's School
11/25 vs. Loomis-Chaffe @ 12:15 am 11/25 vs. Tabor @ 4:00 pm 11/26 vs. St. Paul's School @ 1:00 pm |
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| Wed | Nov | vs. Millbrook | X:30 PM |
| Sat | Dec | @ Hotchkiss | X:30 PM |
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| Mon | Dec | Browse FREE Archive | X:15 PM |
| Sat | Dec | @ Loomis-Chaffee | X:00 PM |
| Fri | Dec 14 - Dec 16 | Lawrenceville Tournament (note) | |
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@ Lawrenceville School
12/15 vs. Lawrenceville @ 9:00 am 12/15 TBA 12/16 TBA |
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| Fri | Dec 28 - Dec 30 | E.G. Watkins-Cushing Academy New Years Tournament (note) | |
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@ Cushing
12/28 vs. Gunnery School @ 1:20 pm 12/29 vs. Govenors Academy @ 11:10 am 12/29 vs. Culver Military Academy @ 7:50 pm 12/30 TBA |
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| Wed | Jan | @ Williston-Northampton | X:30 PM |
| Fri | Jan | vs. Gunnery | X:45 PM |
| Wed | Jan | vs. Choate | X:30 PM |
| Sat | Jan | Albany Academy (note) | X:00 PM |
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@ Berkshire
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| Wed | Jan | @ Westminster | X:30 PM |
| Sat | Jan | vs. Taft | X:30 PM |
| Mon | Jan | @ Millbrook | X:00 PM |
| Sat | Jan | vs. Pomfret | X:30 PM |
| Sun | Jan | vs. Winchendon | X:00 PM |
| Wed | Jan | vs. Berkshire | X:30 PM |
| Wed | Feb | vs. Trinity-Pawling | X:30 PM |
| Sat | Feb | @ Cushing | X:00 PM |
| Wed | Feb | vs. Williston-Northampton | X:30 PM |
| Sat | Feb | vs. Kent | X:00 PM |
| Mon | Feb | @ Gunnery | X:45 PM |
| Wed | Feb | vs. Avon Old Farms | X:30 PM |
| Fri | Feb | @ Salisbury | X:30 PM |
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