| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Wednesday | November 19, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering | |
| Saturday | November 22, 2025 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Saturday | November 22, 2025 | 3:00 PM | 4:00 PM | Game | Sarah W. Gibbons Middle School | vs. Westborough |
| Saturday | November 22, 2025 | 5:00 PM | 6:00 PM | Game | Hopkinton High School | vs. Hopkinton |
| Sunday | November 23, 2025 | 2:00 PM | 3:00 PM | Game | Holliston High School | vs. Holliston |
| Wednesday | December 3, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | December 6, 2025 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | December 7, 2025 | 1:30 PM | 2:30 PM | Game | Sunita L. Williams Elementary School | @ Needham |
| Wednesday | December 10, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | December 13, 2025 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | December 14, 2025 | 11:00 AM | 12:00 PM | Game | Dover-Sherborn High School | vs. Ashland |
| Wednesday | December 17, 2025 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | December 20, 2025 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | December 21, 2025 | 11:40 AM | 12:40 PM | Game | The Roxbury Latin School | @ Parkway |
| Saturday | January 3, 2026 | 4:00 PM | 5:00 PM | Extra-Practice | Kingsbury Club | |
| Sunday | January 4, 2026 | 11:00 AM | 12:00 PM | Game | Dover-Sherborn High School | vs. Holliston |
| Wednesday | January 7, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | January 10, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | January 11, 2026 | 11:30 AM | 12:30 PM | Game | Holbrook Middle-High School | @ Holbrook |
| Wednesday | January 14, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | January 17, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | January 18, 2026 | 12:15 PM | 1:15 PM | Game | DSMS | vs. Westborough |
| Wednesday | January 21, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | January 24, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Wednesday | January 28, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | January 31, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | February 1, 2026 | 1:30 PM | 2:30 PM | Game | Dover-Sherborn High School | vs. Medfield |
| Wednesday | February 4, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | February 7, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | February 8, 2026 | 12:40 PM | 1:40 PM | Game | Medway Middle School | @ Medway |
| Wednesday | February 11, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Sunday | February 15, 2026 | 11:00 AM | 12:00 PM | Game | DSMS | vs. Northboro |
| Saturday | February 21, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Sunday | February 22, 2026 | 11:15 AM | 12:15 PM | Game | Milton Academy | @ Milton |
| Wednesday | February 25, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | February 28, 2026 | 1:00 PM | 2:20 PM | Extra-Practice | Dover-Sherborn High School | |
| Saturday | February 28, 2026 | 5:00 PM | 6:00 PM | Game | Pine Hill School | vs. Westwood |
| Sunday | March 1, 2026 | 12:15 PM | 1:15 PM | Game | Dover-Sherborn High School | vs. Hopkinton |
| Wednesday | March 4, 2026 | 7:45 PM | 9:00 PM | Extra-Practice | Chickering School | |
| Saturday | March 7, 2026 | 6:50 PM | 7:50 PM | Game | Dana Barros Basketball Club | vs. Framingham |
| Sunday | March 8, 2026 | 6:25 PM | 7:25 PM | Game | Hopkinton Middle School | vs. Dedham |
| Wednesday | March 11, 2026 | 7:15 PM | 8:30 PM | Extra-Practice | Pine Hill | |
| Thursday | March 12, 2026 | 7:45 PM | 8:45 PM | Game | Fieldhouse Mansfield | vs. Bridgewater |
| Sunday | March 15, 2026 | 6:30 PM | 7:30 PM | Game | Mass Premier Courts | vs. King Phillip |