| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | December 2, 2026 | 1:11 AM | 2:11 AM | Game | Dexter | @ Dexter Southfield School (MA) |
| Wednesday | December 9, 2026 | 1:11 AM | 2:11 AM | Game | Kimball Union | vs. Albany Academy (NY) |
| Friday | December 18, 2026 | 11:00 AM | 12:20 PM | Game | St Andrews | @ St Andrews School Prep (RI) |
| Friday | January 8, 2027 | 6:30 PM | 7:30 PM | Game | Kimball Union | vs. Lawrence Academy (MA) |
| Saturday | January 9, 2027 | 5:00 PM | 6:00 PM | Game | Kimball Union | vs. Dexter Southfield School (MA) |
| Wednesday | January 13, 2027 | 5:00 PM | 6:20 PM | Game | MacDuffie | @ MacDuffie School Prep (MA) |
| Friday | January 15, 2027 | 5:20 PM | 6:20 PM | Game | Springfield Co | vs. Bridgton Academy (ME) |
| Monday | January 18, 2027 | 4:30 PM | 5:30 PM | Game | Kimball Union | vs. New Hampton School A (NH) |
| Wednesday | January 20, 2027 | 5:00 PM | 6:00 PM | Game | Kimball Union | vs. Brewster Academy National (NH) |
| Friday | January 22, 2027 | 4:00 PM | 5:20 PM | Game | Kimball Union | vs. St Andrews School Prep (RI) |
| Monday | January 25, 2027 | 6:00 PM | 7:00 PM | Game | Lawrence Acad | @ Lawrence Academy (MA) |
| Wednesday | January 27, 2027 | 4:00 PM | 5:00 PM | Game | Deerfield | @ Deerfield Academy (MA) |
| Saturday | January 30, 2027 | 5:00 PM | 6:00 PM | Game | St Georges | @ St Georges School (RI) |
| Saturday | February 6, 2027 | 1:11 AM | 2:11 AM | Game | Kimball Union | vs. Winchendon School-NEPSAC (MA) |
| Saturday | February 13, 2027 | 1:11 AM | 2:11 AM | Game | Albany Academy | @ Albany Academy (NY) |
| Wednesday | February 17, 2027 | 4:00 PM | 5:00 PM | Game | Holderness | @ Holderness School (NH) |
| Monday | February 22, 2027 | 6:00 PM | 7:20 PM | Game | Kimball Union | vs. MacDuffie School Prep (MA) |
| Saturday | February 27, 2027 | 1:11 AM | 2:11 AM | Game | Winchendon | @ Winchendon School-NEPSAC (MA) |