March 15, 2009
| Date | Opponent | Time | |
|---|---|---|---|
| Wed | Dec 3 | @ Canterbury | 2:00 PM |
| Sat | Dec 6 | vs. Winchendon | 6:00 PM |
| Mon | Dec 8 | vs. Kent | 5:15 PM |
| Wed | Dec 10 | vs. Portledge | 5:15 PM |
| Sun | Dec 28 | @ St. Francis Prep | 12:00 AM |
| Mon | Dec 29 | vs. Belmont Hill | 12:00 AM |
| Mon | Dec 29 | vs. Frederick Gunn School | 12:00 AM |
| Tue | Dec 30 | @ Holy Cross | 12:00 AM |
| Wed | Jan 7 | @ Choate (note) | 4:00 PM |
|
Game will be played at Trinity College
|
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| Sat | Jan 10 | vs. Hotchkiss | 7:00 PM |
| Mon | Jan 12 | @ South Kent | 4:45 PM |
| Sat | Jan 17 | vs. Pomfret | 3:30 PM |
| Sun | Jan 18 | vs. Trinity-Pawling | 12:00 AM |
| Mon | Jan 19 | vs. Westminster | 5:00 PM |
| Wed | Jan 21 | vs. Frederick Gunn School | 3:00 PM |
| Sat | Jan 24 | @ Winchendon | 5:00 PM |
| Mon | Jan 26 | vs. Canterbury | 4:30 PM |
| Fri | Jan 30 | vs. Salisbury | 5:00 PM |
| Sun | Feb 1 | vs. Albany Academy | 2:00 PM |
| Wed | Feb 4 | @ Frederick Gunn School | 3:00 PM |
| Wed | Feb 11 | @ Albany Academy | 4:00 PM |
| Fri | Feb 13 | vs. Williston Northampton | 12:00 AM |
| Sat | Feb 14 | @ Williston Northampton | 4:00 PM |
| Mon | Feb 16 | @ Berkshire | 5:15 PM |
| Wed | Feb 18 | vs. Trinity-Pawling | 2:30 PM |
| Sat | Feb 21 | @ Pomfret | 5:30 PM |
| Wed | Feb 25 | vs. Berkshire | 2:00 PM |
| Fri | Feb 27 | vs. Portledge | 12:00 AM |
| Sat | Feb 28 | @ Trinity-Pawling | 12:00 AM |
| Sat | Feb 28 | vs. The Hill School | 12:00 AM |
|
