| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Friday | December 4, 2026 | 5:00 PM | 6:20 PM | Game | Trinity-Pwlng | @ Trinity-Pawling School (NY) |
| Sunday | December 6, 2026 | TBD | TBD | Game | Dana Barrows | @ ZG Prep Showcase TBA |
| Monday | December 7, 2026 | 5:00 PM | 6:00 PM | Game | Salisbury | @ Salisbury School (CT) |
| Wednesday | December 9, 2026 | 3:30 PM | 4:00 PM | Game | Hotchkiss | vs. Suffield Academy (CT) |
| Thursday | December 17, 2026 | 1:11 AM | 2:11 AM | Game | St Joes | @ TBA |
| Friday | December 18, 2026 | 1:11 AM | 2:11 AM | Game | St Joes | @ TBA |
| Wednesday | January 6, 2027 | 2:30 PM | 3:30 PM | Game | Hotchkiss | vs. Millbrook School (NY) |
| Saturday | January 9, 2027 | 1:11 AM | 2:11 AM | Game | St Pauls | @ St Paul’s School (NH) |
| Sunday | January 10, 2027 | 1:11 AM | 2:31 AM | Game | St Francis | vs. Blair Academy (NJ) |
| Wednesday | January 13, 2027 | 4:00 PM | 5:00 PM | Game | Hotchkiss | vs. Kingswood-Oxford School (CT) |
| Friday | January 15, 2027 | 6:00 PM | 7:00 PM | Game | Avon Old Farms | @ Avon Old Farms School (CT) |
| Sunday | January 17, 2027 | 1:11 AM | 2:11 AM | Game | AIC | vs. Taft School (CT) |
| Wednesday | January 20, 2027 | 4:30 PM | 5:30 PM | Game | Canterbury | @ Canterbury School (CT) |
| Saturday | January 23, 2027 | 3:30 PM | 4:30 PM | Game | Westminster | @ Westminster School (CT) |
| Wednesday | January 27, 2027 | 2:30 PM | 3:30 PM | Game | Kent | @ Kent School (CT) |
| Saturday | January 30, 2027 | 4:30 PM | 5:30 PM | Game | Williston | @ Williston Northampton School (MA) |
| Monday | February 1, 2027 | 5:00 PM | 6:00 PM | Game | Hotchkiss | vs. Trinity-Pawling School (NY) |
| Wednesday | February 3, 2027 | 3:00 PM | 4:00 PM | Game | Taft | @ Taft School (CT) |
| Friday | February 5, 2027 | 5:00 PM | 6:00 PM | Game | Brunswick | @ Brunswick School (CT) |
| Wednesday | February 10, 2027 | 4:30 PM | 5:30 PM | Game | Hotchkiss | vs. Dexter Southfield School (MA) |
| Monday | February 15, 2027 | 5:00 PM | 6:00 PM | Game | Berkshire | @ Berkshire School (MA) |
| Wednesday | February 17, 2027 | 5:30 PM | 6:30 PM | Game | Hotchkiss | vs. Avon Old Farms School (CT) |
| Saturday | February 20, 2027 | 3:30 PM | 4:30 PM | Game | Choate | @ Choate Rosemary Hall (CT) |
| Wednesday | February 24, 2027 | 2:30 PM | 3:30 PM | Game | Hotchkiss | vs. Kent School (CT) |
| Saturday | February 27, 2027 | 3:00 PM | 4:00 PM | Game | Loomis | @ Loomis Chaffee School (CT) |
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