March 13, 2020
      
| Date | Opponent | Time | |
|---|---|---|---|
| Fri | Nov 15 | @ Pingree(S) | 5:15 PM | 
| Sun | Nov 17 | Lawrenceville (note) | 10:00 AM | 
| 
                           @ PEA 
                         | 
                      |||
| Fri | Dec 6 | @ Kents Hill | 6:00 PM | 
| Wed | Dec 11 | vs. Pingree | 4:15 PM | 
| Fri | Dec 13 | vs. Middlesex | 4:45 PM | 
| Wed | Dec 18 | vs. Brewster Academy | 4:15 PM | 
| Fri | Dec 20 | @ Brooks | 4:00 PM | 
| Fri | Dec 20- Dec 22 | Brooks-Pingree Holiday Tournament (note) | |
| 
               (@ Brooks) 
             | 
          |||
| Sat | Dec 21 | vs. Millbrook | 11:00 AM | 
| Sat | Dec 21 | Tilton | 5:00 PM | 
| Sun | Dec 22 | Hebron | 9:00 AM | 
| Sat | Dec 28 | vs. North Yarmouth Academy | 1:00 PM | 
| Sat | Dec 28- Dec 29 | Roxbury Latin Showcase (note) | |
| 
               (@ BB&N) 
             | 
          |||
| Sun | Dec 29 | Roxbury Latin | 9:00 AM | 
| Sun | Dec 29 | @ BB&N | 4:00 PM | 
| Sat | Jan 4 | @ North Yarmouth Academy | 3:15 PM | 
| Sat | Jan 11 | @ Portsmouth Abbey | 3:00 PM | 
| Sat | Jan 18 | @ Brewster Academy | 2:30 PM | 
| Mon | Jan 20 | @ Exeter (note) | 5:15 PM | 
| 
                           (rescheduled from Jan 13) 
                         | 
                      |||
| Wed | Jan 22 | vs. Kents Hill | 4:30 PM | 
| Sat | Jan 25 | @ Pingree | 4:15 PM | 
| Wed | Jan 29 | @ St. Paul's | 5:45 PM | 
| Fri | Jan 31 | vs. Hebron | 4:15 PM | 
| Wed | Feb 5 | @ Tilton | 4:45 PM | 
| Sat | Feb 8 | @ St. George's | 4:00 PM | 
| Wed | Feb 12 | @ Hebron | 4:30 PM | 
| Sat | Feb 15 | @ Proctor | 2:15 PM | 
| Wed | Feb 19 | vs. Dexter | 4:00 PM | 
| Fri | Feb 21 | @ St. Mark's | 5:30 PM | 
| Mon | Feb 24 | vs. Belmont Hill | 3:30 PM | 
| Wed | Feb 26 | vs. Holderness | 4:15 PM | 
| Fri | Feb 28 | @ Governor's | 5:15 PM | 
| Wed | Mar 4 | TBD (note) | 12:00 PM | 
| 
                           NEPSAC 
                         | 
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| Sat | Mar 7 | TBD (note) | 12:00 PM | 
| 
                           NEPSAC 
                         | 
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| Sun | Mar 8 | TBD (note) | 12:00 PM | 
| 
                           NEPSAC 
                         | 
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