March 14, 2020
      
| Date | Opponent | Time | |
|---|---|---|---|
| Wed | Nov 20 | vs. TBA(S) (note) | 3:00 PM | 
| Jamboree, Choate, Loomis & Westy | |||
| Wed | Dec 4 | vs. Millbrook | 5:15 PM | 
| Sat | Dec 7 | vs. Lawrenceville | 5:00 PM | 
| Mon | Dec 9 | @ Frederick Gunn School | 5:00 PM | 
| Wed | Dec 11 | @ Berkshire | 4:30 PM | 
| Thu | Dec 19 | Choate | 8:00 AM | 
| Thu | Dec 19 | Tabor | 1:45 PM | 
| Thu | Dec 19- Dec 21 | Taft Holiday Tournament | |
| Fri | Dec 20 | Andover | 8:00 AM | 
| Mon | Jan 6 | vs. The Hill School | 4:00 PM | 
| Wed | Jan 8 | vs. Kent | 2:30 PM | 
| Sat | Jan 11 | vs. Westminster | 4:30 PM | 
| Wed | Jan 15 | vs. Pomfret | 3:30 PM | 
| Sat | Jan 18 | @ Choate | 4:00 PM | 
| Sun | Jan 19 | vs. Worcester Academy | 12:00 PM | 
| Wed | Jan 22 | vs. Loomis Chaffee | 2:45 PM | 
| Sat | Jan 25 | vs. Deerfield | 2:00 PM | 
| Wed | Jan 29 | @ Canterbury | 2:30 PM | 
| Wed | Feb 5 | @ Williston Northampton | 4:30 PM | 
| Wed | Feb 12 | @ Greenwich Academy | 3:30 PM | 
| Sat | Feb 15 | vs. Hotchkiss | 2:30 PM | 
| Wed | Feb 19 | @ Westminster | 3:30 PM | 
| Sat | Feb 22 | vs. Choate | 2:00 PM | 
| Wed | Feb 26 | vs. Berkshire | 2:30 PM | 
| Sat | Feb 29 | @ Hotchkiss | 2:30 PM | 
| 
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