| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | November 19, 2025 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | November 22, 2025 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Wednesday | December 3, 2025 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | December 6, 2025 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | December 7, 2025 | 8:30 AM | 9:30 AM | Game | W L Chenery Upper Elementary School | @ Belmont (White) D5W |
| Wednesday | December 10, 2025 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | December 13, 2025 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | December 14, 2025 | 12:45 PM | 1:45 PM | Game | Trottier Middle School | @ Southboro (Gold) D5T |
| Wednesday | December 17, 2025 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | December 20, 2025 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | December 21, 2025 | 12:15 PM | 1:15 PM | Game | Dover Sherborn Middle School | vs. Arlington (White) D5W |
| Sunday | January 4, 2026 | 8:10 AM | 9:10 AM | Game | Robert Adams Middle School | @ Holliston (Ennis) D5T |
| Wednesday | January 7, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | January 10, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | January 11, 2026 | 10:00 AM | 11:00 AM | Game | McCall Middle School | @ Winchester (BLACK) D5W |
| Wednesday | January 14, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | January 17, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Wednesday | January 21, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | January 24, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Wednesday | January 28, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | January 31, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Saturday | January 31, 2026 | 1:15 PM | 3:15 PM | Other | Case Gymnasium | |
| Sunday | February 1, 2026 | 3:40 PM | 4:40 PM | Game | Kennedy Middle School | @ @Natick D5T |
| Wednesday | February 4, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | February 7, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Saturday | February 7, 2026 | 3:40 PM | 4:40 PM | Game | DSMS | vs. DS |
| Sunday | February 8, 2026 | 12:15 PM | 1:15 PM | Game | Dover Sherborn Middle School | vs. Newton (ORANGE) D5W |
| Wednesday | February 11, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | February 14, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Saturday | February 21, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | February 22, 2026 | 4:15 PM | 5:15 PM | Game | Wayland High School | @ Wayland (Orange) D5W |
| Wednesday | February 25, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | February 28, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Sunday | March 1, 2026 | 11:00 AM | 12:00 PM | Game | Dover Sherborn Middle School | vs. Southboro (White) D5T |
| Sunday | March 1, 2026 | 4:00 PM | 5:00 PM | Game | DSMS | vs. Wellesley |
| Wednesday | March 4, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Saturday | March 7, 2026 | 8:00 AM | 9:15 AM | Practice | Pine Hill Elementary | |
| Saturday | March 7, 2026 | 5:40 PM | 6:40 PM | Game | Dana Barros Basketball Club | @ Game 1 of playoffs: vs. Holliston (Ennis) D5T |
| Sunday | March 8, 2026 | 6:25 PM | 7:25 PM | Game | Elmwood School | @ Game 2 of playoffs |
| Wednesday | March 11, 2026 | 6:00 PM | 7:00 PM | Practice | Pine Hill Elementary | |
| Thursday | March 12, 2026 | 6:30 PM | 7:30 PM | Game | Dana Barros Basketball Club | @ Game 3 of playoffs |
| Saturday | March 14, 2026 | 1:50 PM | 2:50 PM | Game | Dana Barros Basketball Club | @ Game 4 of Playoffs |
| Sunday | March 15, 2026 | 11:00 AM | 12:00 PM | Game | Dana Barros Basketball Club | @ Playoff Championship! |