| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | November 19, 2025 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | November 22, 2025 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Wednesday | December 3, 2025 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | December 6, 2025 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | December 7, 2025 | 4:00 PM | 4:45 PM | Game | Dover-Sherborn High School | vs. Wayland ( Orange) D5W |
| Wednesday | December 10, 2025 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | December 13, 2025 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | December 14, 2025 | 10:50 AM | 11:35 AM | Game | Robert Adams Middle School | vs. Holliston (Ennis) D5T |
| Wednesday | December 17, 2025 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | December 20, 2025 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | December 21, 2025 | 9:45 AM | 10:30 AM | Game | DSMS | vs. Belmont (White) |
| Sunday | January 4, 2026 | 12:50 PM | 1:35 PM | Game | Weston Middle School | vs. Weston D5W |
| Wednesday | January 7, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | January 10, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | January 11, 2026 | 8:30 AM | 9:15 AM | Game | DSMS | vs. Arlington (White) D5W |
| Wednesday | January 14, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill elementary | |
| Saturday | January 17, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Wednesday | January 21, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | January 24, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | January 25, 2026 | 8:30 AM | 9:15 AM | Game | DSMS | vs. Winchester (Black) D5W |
| Wednesday | January 28, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | January 31, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Saturday | January 31, 2026 | 2:00 PM | 4:00 PM | Other | Case Gymnasium | |
| Sunday | February 1, 2026 | 9:45 AM | 10:30 AM | Game | DSMS | vs. Southboro (Gold) D5T |
| Wednesday | February 4, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | February 7, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Saturday | February 7, 2026 | 3:40 PM | 4:40 PM | Game | DSMS | vs. DS Schaefers |
| Wednesday | February 11, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | February 14, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | February 15, 2026 | 11:30 AM | 12:15 PM | Game | Trottier Middle School | vs. Southboro (White) D5T |
| Saturday | February 21, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | February 22, 2026 | 2:10 PM | 2:55 PM | Game | Natick Community-Senior Center | vs. Natick D5T |
| Wednesday | February 25, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Saturday | February 28, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill Elementary | |
| Sunday | March 1, 2026 | 2:45 PM | 3:30 PM | Game | DSMS | vs. Wellesley |
| Wednesday | March 4, 2026 | 6:00 PM | 7:00 PM | Extra-Practice | Pine Hill Elementary | |
| Thursday | March 5, 2026 | 6:00 PM | 7:00 PM | Game | Trottier Middle School | vs. Southboro Gold |
| Saturday | March 7, 2026 | 8:00 AM | 9:15 AM | Extra-Practice | Pine Hill | |
| Sunday | March 8, 2026 | 3:45 PM | 4:30 PM | Game | Massachusetts | vs. Wayland |