| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | December 2, 2023 | 3:30 PM | 4:30 PM | Game | Belmont Hill | @ Belmont Hill School (MA) |
| Wednesday | December 6, 2023 | 5:00 PM | 6:00 PM | Game | Nobles | @ Noble and Greenough School (MA) |
| Saturday | December 9, 2023 | 4:30 PM | 5:30 PM | Game | St Pauls | @ Thayer Academy (MA) |
| Friday | December 15, 2023 | 12:00 AM | 1:00 AM | Game | St Sebastians | @ Taft School (CT) |
| Saturday | December 16, 2023 | 12:15 PM | 1:15 PM | Game | St Sebastians | vs. Brunswick School (CT) |
| Saturday | January 6, 2024 | 4:00 PM | 5:00 PM | Game | Cross Arena | vs. Kimball Union Academy (NH) |
| Wednesday | January 10, 2024 | 4:00 PM | 5:00 PM | Game | St Pauls | vs. Tilton School (NH) |
| Friday | January 12, 2024 | 5:30 PM | 6:30 PM | Game | St Pauls | vs. Brewster Academy Prep (NH) |
| Saturday | January 13, 2024 | 3:30 PM | 4:30 PM | Game | Austin Prep | @ Austin Prep (MA) |
| Wednesday | January 17, 2024 | 4:30 PM | 5:30 PM | Game | St Pauls | @ Holderness School (NH) |
| Saturday | January 20, 2024 | 4:30 PM | 5:30 PM | Game | Loomis | @ Loomis Chaffee School (CT) |
| Wednesday | January 24, 2024 | 3:45 PM | 4:45 PM | Game | St Pauls | vs. Proctor Academy (NH) |
| Friday | January 26, 2024 | 5:30 PM | 6:30 PM | Game | Groton | vs. Groton School (MA) |
| Saturday | January 27, 2024 | 4:00 PM | 5:00 PM | Game | St Pauls | vs. Vermont Academy |
| Wednesday | January 31, 2024 | 4:15 PM | 5:15 PM | Game | St Pauls | @ Phillips Exeter Academy (NH) |
| Friday | February 2, 2024 | 4:30 PM | 5:30 PM | Game | Dexter | vs. Dexter Southfield School (MA) |
| Wednesday | February 7, 2024 | 2:45 PM | 3:45 PM | Game | St Pauls | vs. New Hampton School A (NH) |
| Friday | February 9, 2024 | 6:30 PM | 7:30 PM | Game | St Pauls | @ Williston Northampton School (MA) |
| Wednesday | February 14, 2024 | 3:30 PM | 4:30 PM | Game | St Pauls | vs. Phillips Academy (Andover, MA) |
| Friday | February 16, 2024 | 6:30 PM | 7:30 PM | Game | Deerfield | @ Deerfield Academy (MA) |
| Saturday | February 17, 2024 | 3:00 PM | 4:00 PM | Game | St Pauls | vs. Milton Academy (MA) |
| Wednesday | February 21, 2024 | 4:00 PM | 5:00 PM | Game | BB&N School | vs. Buckingham, Browne & Nichols (MA) |
| Friday | February 23, 2024 | 6:00 PM | 7:00 PM | Game | St Sebastians | @ St Sebastians School (MA) |