| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Friday | December 4, 2026 | 8:00 PM | 9:00 PM | Game | Dana Barros | @ Kent School (CT) |
| Saturday | December 5, 2026 | 1:30 PM | 2:30 PM | Game | Dana Barros | @ St Andrews School Prep (RI) |
| Wednesday | December 9, 2026 | 1:11 AM | 2:11 AM | Game | St Georges | @ St Georges School (RI) |
| Friday | December 11, 2026 | 5:00 PM | 6:00 PM | Game | Holy Cross | @ Deerfield Academy (MA) |
| Saturday | December 12, 2026 | 1:00 PM | 2:00 PM | Game | St Sebastians | vs. Tabor Academy (MA) |
| Thursday | December 17, 2026 | 1:11 AM | 2:11 AM | Game | TBD | @ TBA |
| Friday | December 18, 2026 | 4:00 PM | 5:20 PM | Game | St Sebastians | vs. Trinity-Pawling School (NY) |
| Saturday | December 19, 2026 | 1:11 AM | 2:11 AM | Game | TBD | @ TBA |
| Sunday | January 3, 2027 | 1:11 AM | 2:11 AM | Game | Belmont Hill | @ Berkshire School (MA) |
| Wednesday | January 6, 2027 | 1:11 AM | 2:11 AM | Game | Roxbury | @ Roxbury Latin School (MA) |
| Friday | January 8, 2027 | 1:11 AM | 2:11 AM | Game | St Sebastians | vs. Phillips Exeter Academy (NH) |
| Saturday | January 16, 2027 | 1:11 AM | 2:11 AM | Game | St Sebastians | vs. Groton School (MA) |
| Friday | January 22, 2027 | 1:11 AM | 2:11 AM | Game | Thayer | @ Thayer Academy (MA) |
| Saturday | January 23, 2027 | 2:30 PM | 3:30 PM | Game | Brooks | @ Brooks School (MA) |
| Wednesday | January 27, 2027 | 1:11 AM | 2:11 AM | Game | St Sebastians | vs. Noble & Greenough School (MA) |
| Friday | January 29, 2027 | 5:00 PM | 6:00 PM | Game | Belmont Hill | @ Belmont Hill School (MA) |
| Wednesday | February 3, 2027 | 5:00 PM | 6:00 PM | Game | BB&N School | @ Buckingham, Browne & Nichols (MA) |
| Friday | February 5, 2027 | 1:11 AM | 2:11 AM | Game | St Sebastians | vs. Rivers School (MA) |
| Saturday | February 6, 2027 | 1:11 AM | 2:11 AM | Game | Suffield | @ Suffield Academy (CT) |
| Wednesday | February 10, 2027 | 1:11 AM | 2:11 AM | Game | St Marks | @ St Marks School (MA) |
| Friday | February 12, 2027 | 1:11 AM | 2:11 AM | Game | St Sebastians | vs. Middlesex School (MA) |
| Wednesday | February 17, 2027 | 4:00 PM | 5:00 PM | Game | Lawrence Acad | @ Lawrence Academy (MA) |
| Saturday | February 20, 2027 | 1:00 PM | 2:00 PM | Game | St Sebastians | vs. Governors Academy (MA) |
| Wednesday | February 24, 2027 | 5:00 PM | 6:00 PM | Game | St Sebastians | vs. Milton Academy (MA) |
| Friday | February 26, 2027 | 1:11 AM | 2:11 AM | Game | St Pauls | @ St Paul’s School (NH) |