| Date | Opponent | Time | |
| Sat | Nov 24 - Nov 24 | Belmont Hill Jamboree | |
| Wed | Nov | @ New Hampton School | X:00 PM |
| Fri | Nov | @ Cushing | X:30 PM |
| Sat | Dec | vs. St. Mark's | X:30 PM |
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| Wed | Dec | Browse FREE Archive | X:30 PM |
| Sat | Dec 8 - Jan 9 | ALbany Academy Rider Cup | |
| Fri | Dec 14 - Dec 16 | St. Sebastian's Tournament | |
| Sat | Dec | Northwood Prep | X:00 PM |
| Tue | Jan | Milton | X:00 AM |
| Tue | Jan 1 - Jan 2 | Tabor New Year's Tournament | |
| Wed | Jan | Berwick | X:00 PM |
| Sat | Jan | @ Gunnery | X:30 PM |
| Fri | Jan | @ Williston-Northampton | X:30 PM |
| Sat | Jan | @ Gunnery (note) | X:00 PM |
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Game held at Berkshire.
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| Wed | Jan | vs. Pomfret | X:00 PM |
| Sat | Jan | @ Millbrook | X:00 PM |
| Wed | Jan | vs. Andover | X:30 PM |
| Sun | Jan | @ Canterbury | X:00 PM |
| Wed | Jan | vs. Hoosac | X:00 PM |
| Fri | Feb | vs. New Hampton School | X:00 PM |
| Sat | Feb | vs. Albany Academy | X:00 PM |
| Wed | Feb | @ Brewster Academy | X:00 PM |
| Fri | Feb | vs. Vermont Academy | X:00 PM |
| Wed | Feb | @ Holderness | X:30 PM |
| Tue | Feb | @ Kimball Union | X:30 PM |
| Fri | Feb | vs. Williston-Northampton | X:00 PM |
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