| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | December 3, 2025 | 5:00 PM | 6:10 PM | Game | Exeter | @ Phillips Exeter Academy (NH) |
| Sunday | December 7, 2025 | 3:00 PM | 4:10 PM | Game | Dana Barros | @ Greenwich Country Day School (CT) |
| Wednesday | December 10, 2025 | 4:30 PM | 5:40 PM | Game | Govenors | @ Governors Academy (MA) |
| Friday | December 12, 2025 | 6:15 PM | 7:25 PM | Game | TBD | vs. Buckingham, Browne & Nichols (MA) |
| Friday | December 19, 2025 | 1:11 AM | 2:21 AM | Game | Middlesex | vs. St Lukes School (CT) |
| Friday | December 19, 2025 | 6:30 PM | 7:40 PM | Game | Middlesex | vs. Holderness School (NH) |
| Wednesday | January 14, 2026 | 3:30 PM | 4:40 PM | Game | St Marks | @ St Marks School (MA) |
| Wednesday | January 21, 2026 | 5:00 PM | 6:10 PM | Game | Nobles | @ Noble and Greenough School (MA) |
| Saturday | January 24, 2026 | 2:00 PM | 3:10 PM | Game | Milton Acad | @ Milton Academy (MA) |
| Wednesday | January 28, 2026 | 5:00 PM | 6:10 PM | Game | Middlesex | vs. Roxbury Latin School (MA) |
| Friday | February 6, 2026 | 4:30 PM | 5:40 PM | Game | Middlesex | vs. Brooks School (MA) |
| Friday | February 6, 2026 | 4:30 PM | 5:40 PM | Game | Lawrence Acad | @ Lawrence Academy (MA) |
| Wednesday | February 11, 2026 | 5:00 PM | 6:10 PM | Game | Thayer | @ Thayer Academy (MA) |
| Wednesday | February 18, 2026 | 3:00 PM | 4:10 PM | Game | Middlesex | vs. Groton School (MA) |
| Friday | February 20, 2026 | 5:00 PM | 6:10 PM | Game | Middlesex | vs. Belmont Hill School (MA) |
| Saturday | February 21, 2026 | 1:11 AM | 2:21 AM | Game | Middlesex | vs. Proctor Academy (NH) |
| Wednesday | February 25, 2026 | 5:00 PM | 6:10 PM | Game | Middlesex | vs. Tabor Academy (MA) |
| Saturday | February 28, 2026 | 1:30 PM | 2:40 PM | Game | St Georges | @ St Georges School (RI) |