March 14, 2024
      
| Date | Opponent | Time | |
|---|---|---|---|
| Mon | Nov 27 | Frederick Gunn School(S) (note) | 10:00 AM | 
| Piatelli Jamboree at Hotchkiss School | |||
| Mon | Nov 27 | Dexter(S) (note) | 1:30 PM | 
| Piatelli Jamboree at Hotchkiss School | |||
| Wed | Nov 29 | @ Millbrook | 2:30 PM | 
| Sat | Dec 2 | vs. Hotchkiss | 3:30 PM | 
| Mon | Dec 4 | vs. Berkshire | 5:15 PM | 
| Sat | Dec 9 | vs. Loomis Chaffee | 7:00 PM | 
| Wed | Dec 13 | vs. Salisbury | 2:30 PM | 
| Fri | Dec 15 | Kents Hill (note) | 7:00 PM | 
| @ St. Mark's | |||
| Fri | Dec 15- Dec 16 | William Barber Memorial Tournament | |
| Thu | Dec 28- Dec 30 | E.G. Watkins-Cushing Academy New Years Tournament | |
| Sat | Dec 30 | Governor's | 9:00 AM | 
| Wed | Jan 3 | @ Williston Northampton | 2:30 PM | 
| Fri | Jan 5 | Worcester Academy (note) | 4:00 PM | 
| @ Worcester Center | |||
| Sat | Jan 6 | Lawrence Academy (note) | 1:00 PM | 
| @ Worcester Center | |||
| Wed | Jan 10 | vs. Choate | 4:45 PM | 
| Fri | Jan 12 | @ Frederick Gunn School | 7:00 PM | 
| Wed | Jan 17 | vs. Westminster | 2:30 PM | 
| Sat | Jan 20 | @ Taft | 4:15 PM | 
| Mon | Jan 22 | vs. Millbrook | 5:15 PM | 
| Wed | Jan 24 | vs. Albany Academy | 4:30 PM | 
| Sat | Jan 27 | @ Pomfret | 3:15 PM | 
| Sun | Jan 28 | @ Winchendon | 1:00 PM | 
| Wed | Jan 31 | @ Berkshire | 2:30 PM | 
| Wed | Feb 7 | vs. Trinity-Pawling | 2:30 PM | 
| Sat | Feb 10 | @ Cushing | 3:00 PM | 
| Mon | Feb 12 | vs. Frederick Gunn School | 5:00 PM | 
| Wed | Feb 14 | vs. Williston Northampton | 4:00 PM | 
| Sat | Feb 17 | @ Kent | 7:00 PM | 
| Wed | Feb 21 | @ Avon Old Farms | 2:30 PM | 
| Sat | Feb 24 | vs. Wilbraham & Monson | 2:30 PM | 
| Wed | Feb 28 | Tilton (note) | 4:00 PM | 
| @ Trinity College | |||
| Sat | Mar 2 | vs. Pomfret | 2:00 PM | 
| Sun | Mar 3 | Rivers (note) | 12:00 PM | 
| @Harvard University | |||
| 
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