| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | November 21, 2026 | 11:00 AM | 12:00 PM | Game | Avon Old Farms | @ Avon Old Farms School (CT) |
| Friday | December 11, 2026 | 1:11 AM | 2:11 AM | Game | Berkshire | @ Berkshire School (MA) |
| Sunday | December 13, 2026 | 1:11 AM | 2:11 AM | Game | Holy Cross | @ St Georges School (RI) |
| Wednesday | December 16, 2026 | 5:00 PM | 6:00 PM | Game | TBD | vs. Lawrence Academy (MA) |
| Friday | January 8, 2027 | 6:00 PM | 7:00 PM | Game | Cheshire | vs. Brunswick School (CT) |
| Saturday | January 30, 2027 | 1:11 AM | 2:11 AM | Game | Cheshire | vs. Albany Academy (NY) |
| Wednesday | February 3, 2027 | 3:00 PM | 4:20 PM | Game | Cheshire | vs. MacDuffie School Prep (MA) |
| Wednesday | February 10, 2027 | 1:11 AM | 2:11 AM | Game | St Lukes | @ St Lukes School (CT) |
| Saturday | February 20, 2027 | 1:11 AM | 2:11 AM | Game | Winchendon | @ Winchendon School-NEPSAC (MA) |
| Wednesday | February 24, 2027 | 1:11 AM | 2:31 AM | Game | Cheshire | vs. Darrow School AA (NY) |
| Wednesday | February 24, 2027 | 5:00 PM | 6:20 PM | Game | St Andrews | @ St Andrews School Prep (RI) |