March 15, 2009
| Date | Opponent | Time | |
|---|---|---|---|
| Sat | Nov 22 | vs. Brewster Academy | 1:00 PM |
| Mon | Dec 1 | @ Frederick Gunn School(S) | 12:00 AM |
| Wed | Dec 3 | vs. Worcester Academy | 5:00 PM |
| Sat | Dec 6 | @ Westminster | 6:00 PM |
| Wed | Dec 10 | @ Deerfield | 6:00 PM |
| Fri | Dec 12 | @ Williston Northampton | 5:30 PM |
| Sat | Dec 13 | @ Holderness | 5:00 PM |
| Sat | Dec 20 | vs. Choate (note) | 11:00 AM |
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Lawrenceville Tourn. at Princeton University
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| Sat | Dec 20 | vs. Upper Canada College (note) | 4:00 PM |
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Lawrenceville Tourn
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| Sun | Dec 21 | vs. Nichols (note) | 8:00 PM |
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Lawrenceville
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| Thu | Jan 1 | vs. Lawrence Academy (note) | 9:00 AM |
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Cushing Tournament
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| Thu | Jan 1 | vs. Pomfret | 5:45 PM |
| Fri | Jan 2 | @ Cushing (note) | 3:30 PM |
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Watkins Tournament
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| Sat | Jan 3 | vs. Canterbury | 12:00 AM |
| Sat | Jan 10 | vs. Proctor | 4:30 PM |
| Wed | Jan 14 | vs. Stanstead College | 4:30 PM |
| Sat | Jan 17 | vs. Holderness | 4:00 PM |
| Sun | Jan 18 | vs. Choate | 2:30 PM |
| Wed | Jan 21 | @ Avon Old Farms | 4:00 PM |
| Sat | Jan 24 | vs. Lawrenceville | 2:00 PM |
| Sun | Jan 25 | vs. Taft | 1:30 PM |
| Tue | Jan 27 | vs. Cushing | 12:00 AM |
| Sat | Jan 31 | vs. Tilton | 3:30 PM |
| Sun | Feb 1 | @ Tilton | 2:30 PM |
| Wed | Feb 4 | vs. Kimball Union | 3:00 PM |
| Fri | Feb 6 | vs. Winchendon | 7:00 PM |
| Sat | Feb 7 | @ Tabor | 4:00 PM |
| Wed | Feb 11 | vs. Williston Northampton | 2:30 PM |
| Sat | Feb 14 | @ Exeter | 4:00 PM |
| Wed | Feb 18 | vs. Exeter | 2:00 PM |
| Fri | Feb 20 | @ Kimball Union | 5:00 PM |
| Sat | Feb 21 | @ Loomis Chaffee | 4:30 PM |
| Wed | Feb 25 | @ Andover | 3:30 PM |
| Sat | Feb 28 | vs. Tabor | 5:00 PM |
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