| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Friday | November 20, 2026 | 1:11 AM | 2:11 AM | Game | Albany Academy | @ Albany Academy (NY) |
| Wednesday | December 2, 2026 | 3:30 PM | 4:30 PM | Game | BB&N School | @ Buckingham, Browne & Nichols (MA) |
| Friday | December 4, 2026 | 5:00 PM | 6:20 PM | Game | Dana Barros | vs. Governors Academy (MA) |
| Saturday | December 5, 2026 | 12:15 PM | 1:35 PM | Game | Dana Barros | @ Deerfield Academy (MA) |
| Wednesday | December 9, 2026 | 3:45 PM | 4:45 PM | Game | Groton | @ Groton School (MA) |
| Sunday | December 13, 2026 | 3:30 PM | 4:30 PM | Game | Holy Cross | vs. Choate Rosemary Hall (CT) |
| Wednesday | December 16, 2026 | 4:00 PM | 5:00 PM | Game | Milton Acad | vs. Phillips Exeter Academy (NH) |
| Friday | January 8, 2027 | 5:00 PM | 6:00 PM | Game | Thayer | @ Thayer Academy (MA) |
| Saturday | January 9, 2027 | 1:00 PM | 2:00 PM | Game | Milton Acad | vs. Belmont Hill School (MA) |
| Sunday | January 10, 2027 | 1:00 PM | 2:00 PM | Game | Avon Old Farms | @ Avon Old Farms School (CT) |
| Wednesday | January 13, 2027 | 3:30 PM | 4:30 PM | Game | Milton Acad | vs. Rivers School (MA) |
| Saturday | January 16, 2027 | 7:00 PM | 8:00 PM | Game | Springfield Co | vs. Loomis Chaffee School (CT) |
| Friday | January 22, 2027 | 4:30 PM | 5:30 PM | Game | Milton Acad | vs. Dexter Southfield School (MA) |
| Monday | January 25, 2027 | 2:00 PM | 3:00 PM | Game | Middlesex | @ Middlesex School (MA) |
| Wednesday | January 27, 2027 | 3:30 PM | 4:30 PM | Game | Milton Acad | vs. Phillips Academy Andover (MA) |
| Saturday | January 30, 2027 | 1:30 PM | 2:30 PM | Game | St Marks | @ St Marks School (MA) |
| Saturday | February 6, 2027 | 5:00 PM | 6:00 PM | Game | Milton Acad | vs. Brooks School (MA) |
| Wednesday | February 10, 2027 | 3:30 PM | 4:30 PM | Game | Milton Acad | vs. Roxbury Latin School (MA) |
| Friday | February 12, 2027 | 6:30 PM | 7:30 PM | Game | Milton Acad | vs. Lawrence Academy (MA) |
| Saturday | February 13, 2027 | 1:00 PM | 2:00 PM | Game | Milton Acad | vs. Buckingham, Browne & Nichols (MA) |
| Wednesday | February 17, 2027 | 6:00 PM | 7:00 PM | Game | St Georges | @ St Georges School (RI) |
| Friday | February 19, 2027 | 6:15 PM | 7:15 PM | Game | Tabor | @ Tabor Academy (MA) |
| Saturday | February 20, 2027 | 4:00 PM | 5:00 PM | Game | Milton Acad | vs. St Paul’s School (NH) |
| Wednesday | February 24, 2027 | 5:00 PM | 6:00 PM | Game | St Sebastians | @ St Sebastians School (MA) |
| Friday | February 26, 2027 | 6:00 PM | 7:00 PM | Game | Milton Acad | vs. Noble & Greenough School (MA) |