March 14, 2019
| Date | Opponent | Time | |
|---|---|---|---|
| Fri | Nov 16 | @ Trinity-Pawling(S) | 6:00 PM |
| Sat | Nov 17 | St. Sebastian's(S) (note) | 2:00 PM |
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Game played at Pomfret
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| Mon | Nov 26 | Canterbury(S) (note) | 10:00 AM |
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Berkshire Jamboree
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| Mon | Nov 26 | Kent(S) (note) | 4:00 PM |
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Berkshire Jamboree
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| Wed | Nov 28 | vs. Hotchkiss | 3:00 PM |
| Sat | Dec 1 | Hebron (note) | 6:30 PM |
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Exeter Showcase
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| Sun | Dec 2 | @ Exeter (note) | 2:30 PM |
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Exeter Showcase
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| Wed | Dec 5 | vs. Berkshire | 2:30 PM |
| Fri | Dec 7 | vs. Kent | 5:00 PM |
| Sat | Dec 8 | @ Williston Northampton | 6:00 PM |
| Thu | Dec 13 | Trinity-Pawling | 1:00 PM |
| Thu | Dec 13- Dec 15 | Avon Old Farms Christmas Classic | |
| Fri | Dec 14 | Kent | 9:00 AM |
| Fri | Dec 14 | Loomis Chaffee | 3:00 PM |
| Sat | Dec 15 | St. Paul's | 3:30 PM |
| Tue | Jan 1 | vs. Pope Francis(S) | 2:00 PM |
| Wed | Jan 2 | North Yarmouth Academy (note) | 3:00 PM |
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Played at Holy Cross
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| Fri | Jan 4 | @ Canterbury | 7:00 PM |
| Sat | Jan 5 | vs. Winchendon | 3:00 PM |
| Mon | Jan 7 | vs. Taft | 5:00 PM |
| Wed | Jan 9 | vs. Hoosac | 3:00 PM |
| Sat | Jan 12 | vs. Stanstead College | 3:00 PM |
| Mon | Jan 14 | vs. Trinity-Pawling | 4:30 PM |
| Wed | Jan 16 | vs. Millbrook | 4:30 PM |
| Sat | Jan 19 | vs. Williston Northampton | 4:30 PM |
| Wed | Jan 23 | vs. Salisbury | 4:00 PM |
| Sat | Jan 26 | @ The Hill School | 5:00 PM |
| Wed | Jan 30 | @ Millbrook | 5:00 PM |
| Wed | Feb 6 | vs. Avon Old Farms | 2:30 PM |
| Fri | Feb 8 | @ Brunswick | 6:00 PM |
| Sat | Feb 9 | vs. Lawrenceville | 5:30 PM |
| Mon | Feb 11 | vs. Canterbury | 5:00 PM |
| Wed | Feb 13 | Pomfret (note) | 1:45 PM |
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Game to be played at Trinity College
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| Fri | Feb 15 | vs. Brunswick | 5:15 PM |
| Mon | Feb 18 | vs. Bishop's College School | 4:30 PM |
| Wed | Feb 20 | vs. Westminster | 4:00 PM |
| Sat | Feb 23 | @ Berkshire | 2:30 PM |
| Wed | Feb 27 | @ Kimball Union | 4:30 PM |
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