March 14, 2020
      
| Date | Opponent | Time | |
|---|---|---|---|
| Mon | Dec 2 | Frederick Gunn School(S) (note) | 10:30 AM | 
| @ Berkshire Jamboree, Berkshire School | |||
| Mon | Dec 2 | Hotchkiss(S) (note) | 12:00 PM | 
| @ Berkshire Jamboree, Berkshire School | |||
| Mon | Dec 2 | vs. Hoosac | 3:00 PM | 
| Sat | Dec 7 | Hebron (note) | 6:30 PM | 
| @ Exeter | |||
| Sun | Dec 8 | Kimball Union (note) | 2:30 PM | 
| @ Exeter | |||
| Wed | Dec 11 | vs. Brunswick | 3:30 PM | 
| Fri | Dec 13 | vs. Frederick Gunn School | 5:00 PM | 
| Sat | Dec 14 | @ Salisbury | 7:00 PM | 
| Thu | Dec 19 | @ Avon Old Farms | 5:00 PM | 
| Thu | Dec 19- Dec 21 | Avon Old Farms Christmas Classic (note) | |
| @ Avon Old Farms | |||
| Fri | Dec 20 | St. Paul's | 11:00 AM | 
| Fri | Dec 20 | Tabor | 7:00 PM | 
| Sat | Dec 21 | Frederick Gunn School | 3:30 PM | 
| Sat | Jan 11 | vs. Loomis Chaffee | 5:30 PM | 
| Mon | Jan 13 | vs. Millbrook | 5:00 PM | 
| Wed | Jan 15 | vs. Trinity-Pawling | 4:00 PM | 
| Mon | Jan 20 | @ Avon Old Farms | 6:00 PM | 
| Wed | Jan 22 | @ Hotchkiss | 2:30 PM | 
| Wed | Jan 29 | @ Taft | 4:30 PM | 
| Sat | Feb 1 | @ Westminster | 4:30 PM | 
| Wed | Feb 5 | vs. Taft | 4:30 PM | 
| Wed | Feb 12 | @ Berkshire | 3:00 PM | 
| Sat | Feb 15 | @ Trinity-Pawling | 7:00 PM | 
| Wed | Feb 19 | vs. Hotchkiss | 4:30 PM | 
| Thu | Feb 20 | vs. Salisbury | 5:00 PM | 
| Sat | Feb 22 | vs. Canterbury | 4:30 PM | 
| Wed | Feb 26 | @ Deerfield | 4:15 PM | 
| Sat | Feb 29 | vs. Choate (note) | 6:30 PM | 
| Alumni Game
 Senior Night | |||
| Wed | Mar 4 | Cushing (note) | 3:30 PM | 
| at Deerfield Academy | |||
| 
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