| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | December 5, 2026 | 3:00 PM | 4:00 PM | Game | Belmont Hill | @ Belmont Hill School (MA) |
| Sunday | December 6, 2026 | 1:11 AM | 2:31 AM | Game | Dana Barros | vs. Loomis Chaffee School (CT) |
| Friday | January 8, 2027 | 6:00 PM | 7:00 PM | Game | St Pauls | vs. Concord Academy (MA) |
| Saturday | January 9, 2027 | 1:11 AM | 2:11 AM | Game | St Pauls | vs. Hotchkiss School (CT) |
| Saturday | January 16, 2027 | 3:30 PM | 4:30 PM | Game | St Pauls | vs. Austin Prep (MA) |
| Wednesday | January 20, 2027 | 5:30 PM | 6:30 PM | Game | Holderness | @ Holderness School (NH) |
| Wednesday | February 10, 2027 | 4:00 PM | 5:00 PM | Game | St Pauls | vs. New Hampton School A (NH) |
| Saturday | February 13, 2027 | 4:00 PM | 5:00 PM | Game | St Pauls | @ Brewster Academy National (NH) |
| Saturday | February 13, 2027 | 4:00 PM | 5:20 PM | Game | Brewster | @ Brewster Academy National (NH) |
| Wednesday | February 17, 2027 | 4:45 PM | 5:45 PM | Game | Andover | @ Phillips Academy Andover (MA) |
| Friday | February 19, 2027 | 6:30 PM | 7:30 PM | Game | St Pauls | vs. Deerfield Academy (MA) |
| Saturday | February 20, 2027 | 4:00 PM | 5:00 PM | Game | Milton Acad | @ Milton Academy (MA) |
| Wednesday | February 24, 2027 | 4:00 PM | 5:00 PM | Game | St Pauls | vs. Buckingham, Browne & Nichols (MA) |
| Friday | February 26, 2027 | 1:11 AM | 2:11 AM | Game | St Pauls | vs. St Sebastians School (MA) |