| Date | Opponent | Time | |
| Sun | Nov | Canterbury (S) (note) | X:15 PM |
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As part of the St. Paul's Jamboree
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| Sun | Nov | @ St. Paul's (S) (note) | X:15 PM |
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as part of the St. Paul's Jamboree
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| Mon | Nov | Tabor (note) | X:00 AM |
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Taking place at the St. Paul's School
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| Wed | Nov | Browse FREE Archive | X:30 PM |
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as part of the Founders League Jamboree
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| Sat | Dec | @ Trinity-Pawling | X:00 PM |
| Wed | Dec | vs. Pomfret | X:30 PM |
| Sat | Dec | vs. Canterbury | X:00 PM |
| Wed | Dec | @ Choate | X:00 PM |
| Thu | Dec 13 - Dec 14 | Avon Old Farms Christmas Classic (note) | |
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12/13 v. Kent @7:00 @AOF
12/14 v. St. Paul's @9:00 AM @AOF 12/14 v. Gunnery @3:00 @ AOF |
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| Sat | Jan | vs. Kent | X:30 PM |
| Wed | Jan | @ Deerfield | X:30 PM |
| Sat | Jan | @ Hotchkiss | X:00 PM |
| Mon | Jan | @ Brunswick | X:00 PM |
| Wed | Jan | @ Taft | X:45 PM |
| Sat | Jan | vs. Westminster | X:30 PM |
| Wed | Jan | @ Avon Old Farms | X:00 PM |
| Thu | Jan | @ Kingswood-Oxford | X:45 PM |
| Sat | Jan | @ Andover | X:15 PM |
| Wed | Jan | @ Williston-Northampton | X:15 PM |
| Wed | Feb | vs. Deerfield | X:00 PM |
| Fri | Feb | vs. Gunnery | X:00 PM |
| Wed | Feb | @ Westminster | X:30 PM |
| Thu | Feb | vs. Salisbury | X:00 PM |
| Sat | Feb | @ Northfield - Mt. Hermon | X:00 PM |
| Wed | Feb | vs. Choate | X:00 PM |
| Sat | Feb | vs. Avon Old Farms | X:00 PM |
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