| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | December 5, 2026 | 4:00 PM | 5:00 PM | Game | Roxbury | @ Roxbury Latin School (MA) |
| Monday | December 7, 2026 | 4:30 PM | 5:30 PM | Game | New Hampton | @ New Hampton School A (NH) |
| Wednesday | December 9, 2026 | 4:00 PM | 5:00 PM | Game | Holderness | vs. Phillips Academy Andover (MA) |
| Saturday | December 12, 2026 | 8:00 PM | 9:20 PM | Game | Holy Cross | vs. St Lukes School (CT) |
| Friday | December 18, 2026 | 2:30 PM | 3:30 PM | Game | Holderness | vs. Buckingham, Browne & Nichols (MA) |
| Saturday | December 19, 2026 | 4:45 PM | 5:45 PM | Game | Middlesex | vs. Greens Farms Academy (CT) |
| Sunday | December 20, 2026 | 11:45 AM | 12:45 PM | Game | Middlesex | vs. Portsmouth Abbey School (RI) |
| Wednesday | January 6, 2027 | 5:00 PM | 6:00 PM | Game | Holderness | vs. Kents Hill School (ME) |
| Saturday | January 9, 2027 | 2:00 PM | 3:00 PM | Game | Pingree | @ Pingree School (MA) |
| Monday | January 11, 2027 | 4:30 PM | 5:30 PM | Game | Holderness | vs. Vermont Academy |
| Wednesday | January 13, 2027 | 4:30 PM | 5:30 PM | Game | Holderness | vs. Brooks School (MA) |
| Saturday | January 16, 2027 | 3:30 PM | 4:30 PM | Game | St Marks | @ St Marks School (MA) |
| Sunday | January 17, 2027 | 1:11 AM | 2:11 AM | Game | AIC | @ TBA |
| Sunday | January 17, 2027 | 9:30 AM | 10:30 AM | Game | TBD | vs. Frederick Gunn School (CT) |
| Wednesday | January 20, 2027 | 5:30 PM | 6:30 PM | Game | Holderness | vs. St Paul’s School (NH) |
| Saturday | January 23, 2027 | 4:00 PM | 5:00 PM | Game | Proctor Acad | @ Proctor Academy (NH) |
| Friday | January 29, 2027 | 5:00 PM | 6:00 PM | Game | Tilton | @ Tilton School (NH) |
| Saturday | January 30, 2027 | 4:30 PM | 5:30 PM | Game | Holderness | vs. Austin Prep (MA) |
| Monday | February 1, 2027 | 4:00 PM | 5:00 PM | Game | Lexington | @ Lexington Christian Academy (MA) |
| Wednesday | February 3, 2027 | 1:11 AM | 2:11 AM | Game | Holderness | vs. Bradford Christian Academy (MA) |
| Friday | February 5, 2027 | 4:30 PM | 5:30 PM | Game | Govenors | @ Governors Academy (MA) |
| Friday | February 12, 2027 | 4:00 PM | 5:00 PM | Game | Holderness | vs. Brewster Academy National (NH) |
| Saturday | February 13, 2027 | 4:00 PM | 5:00 PM | Game | Beaver | @ Beaver Country Day School (MA) |
| Wednesday | February 17, 2027 | 4:00 PM | 5:00 PM | Game | Holderness | vs. Kimball Union Academy (NH) |
| Saturday | February 20, 2027 | 3:30 PM | 4:30 PM | Game | Hyde | @ Hyde School (ME) |
| Friday | February 26, 2027 | 4:00 PM | 5:00 PM | Game | Holderness | vs. Proctor Academy (NH) |
| Saturday | February 27, 2027 | 3:00 PM | 4:00 PM | Game | Holderness | vs. Marianapolis Prep (CT) |