| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Monday | November 17, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Cuniff School | |
| Saturday | November 22, 2025 | 10:00 AM | 11:15 AM | Extra-Practice | Watertown Middle School | |
| Monday | November 24, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Cuniff School | |
| Saturday | November 29, 2025 | 10:00 AM | 11:15 AM | Extra-Practice | Watertown Middle School | |
| Saturday | November 29, 2025 | 3:35 PM | 4:35 PM | Game | Dana Barros Basketball Club | vs. Attleboro |
| Saturday | November 29, 2025 | 5:45 PM | 6:45 PM | Game | Dana Barros Basketball Club | vs. Parkway (West Roxbury) |
| Thursday | December 4, 2025 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Sunday | December 7, 2025 | 1:00 PM | 2:00 PM | Game | Watertown Middle School | vs. Weston |
| Thursday | December 11, 2025 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Sunday | December 14, 2025 | 1:45 PM | 2:45 PM | Game | Wayland High School | @ Wayland |
| Thursday | December 18, 2025 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Saturday | December 20, 2025 | 3:30 PM | 4:30 PM | Game | TBD | @ Bedford |
| Sunday | December 21, 2025 | 7:00 PM | 8:00 PM | Game | Watertown Middle School | vs. Lincoln-Sudbury |
| Sunday | January 4, 2026 | 1:30 PM | 2:30 PM | Game | Robert Adams Middle School | @ Holliston |
| Thursday | January 8, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Saturday | January 10, 2026 | 4:30 PM | 5:30 PM | Game | Watertown Middle School | vs. Belmont |
| Sunday | January 11, 2026 | 10:20 AM | 11:20 AM | Game | Hunnewell Elementary School | @ Wellesley |
| Thursday | January 15, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Saturday | January 17, 2026 | 7:00 PM | 8:00 PM | Game | Watertown Middle School | vs. Winchester |
| Sunday | January 18, 2026 | 1:00 PM | 2:00 PM | Game | Watertown Middle School | vs. Westwood |
| Thursday | January 22, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Thursday | January 29, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Sunday | February 1, 2026 | 12:00 PM | 1:00 PM | Game | Medfield High School | @ Medfield |
| Thursday | February 5, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Sunday | February 8, 2026 | 11:45 AM | 12:45 PM | Game | Stacy Middle School | @ Milford |
| Thursday | February 12, 2026 | 7:15 PM | 8:45 PM | Extra-Practice | Gann Academy | |
| Sunday | February 15, 2026 | 12:10 PM | 1:10 PM | Game | Frederick W. Hartnett Middle School | @ Blackstone-Millville |
| Thursday | February 19, 2026 | 7:45 PM | 9:15 PM | Extra-Practice | Gann Academy | |
| Sunday | February 22, 2026 | 2:10 PM | 3:10 PM | Game | Watertown Middle School | vs. Bedford |
| Thursday | February 26, 2026 | 7:45 PM | 9:15 PM | Extra-Practice | Gann Academy | |
| Sunday | March 1, 2026 | 4:30 PM | 5:30 PM | Game | Watertown Middle School | vs. North Quincy |
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