| Date | Opponent | Time | |
| Mon | Nov 26 - Nov 26 | Berkshire Jamboree (note) | |
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Scrimmage
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| Wed | Nov 28 - Nov 28 | Founder's League Jamboree | |
| Sat | Dec | @ Exeter | X:30 PM |
| Sun | Dec | Berwick | X:00 PM |
| Wed | Dec | @ Brunswick | X:00 PM |
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| Sat | Dec | Browse FREE Archive | X:00 PM |
| Thu | Dec 13 - Dec 14 | Avon Old Farms Christmas Classic (note) | |
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Game vs. Loomis @ Avon 12/13 7pm
Game vs. Gunnery @ Trinity College 12/14 9am Game vs. St. Paul's @ Avon 12/14 5pm |
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| Fri | Dec | Gunnery | X:00 AM |
| Fri | Dec | St. Paul's | X:00 PM |
| Sat | Dec | Berkshire | X:30 PM |
| Sat | Dec 15 - Dec 15 | Avon Christmas Classic | |
| Sat | Jan | @ Loomis-Chaffee | X:30 PM |
| Wed | Jan | @ Trinity-Pawling | X:30 PM |
| Sat | Jan | vs. Avon Old Farms | X:00 PM |
| Mon | Jan | @ Millbrook | X:30 PM |
| Wed | Jan | vs. Hotchkiss | X:30 PM |
| Sat | Jan | @ Salisbury | X:00 PM |
| Mon | Jan | vs. Gunnery | X:30 PM |
| Wed | Jan | vs. Taft | X:30 PM |
| Sat | Jan | vs. Westminster | X:45 PM |
| Wed | Jan | @ Taft | X:30 PM |
| Wed | Feb | vs. Berkshire | X:00 PM |
| Mon | Feb | vs. Brunswick | X:30 PM |
| Wed | Feb | @ Hotchkiss | X:30 PM |
| Sat | Feb | @ Canterbury | X:00 PM |
| Mon | Feb | vs. Trinity-Pawling | X:00 PM |
| Wed | Feb | vs. Deerfield | X:30 PM |
| Sat | Feb | @ Choate | X:00 PM |
| Wed | Feb | Dexter | X:30 PM |
| Fri | Mar | Gunnery | X:30 PM |
| Sun | Mar | Salisbury (note) | X:30 PM |
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NEPSHIA Elite 8 Finals
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