| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | February 19, 2026 | 5:50 PM | 6:40 PM | Practice | Flynn | Mite 1, Mite 2, Mite 3, Mite 4 Black, Mite 4 Red, Squirt 1, Squirt 3, Girls U10 |
| Tuesday | September 8, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3, Girls U10 |
| Thursday | September 10, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Saturday | September 12, 2026 | 1:10 PM | 2:10 PM | Game | Burlington | @ Junior Railers Squirt 1 |
| Sunday | September 13, 2026 | 5:30 PM | 6:30 PM | Game | Malden | vs. Framingham Squirt 2 |
| Tuesday | September 15, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | September 17, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Saturday | September 19, 2026 | 5:00 PM | 6:00 PM | Game | Malden | @ Haverhill Squirt 1 |
| Tuesday | September 22, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Girls U10 |
| Thursday | September 24, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3 |
| Sunday | September 27, 2026 | 10:20 AM | 11:20 AM | Game | Billerica | @ Billerica Squirt 1 |
| Tuesday | September 29, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | October 1, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Saturday | October 3, 2026 | 2:00 PM | 3:00 PM | Game | Wellesley Rink 1 | vs. Wellesley Squirt 2 |
| Sunday | October 4, 2026 | 8:20 AM | 9:20 AM | Game | Burlington | vs. Junior Railers Squirt 1 |
| Tuesday | October 6, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3, Girls U10 |
| Thursday | October 8, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Sunday | October 11, 2026 | 12:30 PM | 1:30 PM | Game | Dorchester | @ Westwood Squirt 2 |
| Tuesday | October 13, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | October 15, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3 |
| Saturday | October 17, 2026 | 2:00 PM | 3:00 PM | Game | Waltham | vs. Waltham Squirt 3 |
| Sunday | October 18, 2026 | 7:10 AM | 8:10 AM | Game | Burlington | @ Parkway Squirt 2 |
| Tuesday | October 20, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Girls U10 |
| Thursday | October 22, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Sunday | October 25, 2026 | 7:00 AM | 8:00 AM | Game | Framingham | vs. Framingham Squirt 2 |
| Tuesday | October 27, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | October 29, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Tuesday | November 3, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3, Girls U10 |
| Thursday | November 5, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3 |
| Tuesday | November 10, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | November 12, 2026 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Tuesday | November 17, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Girls U10 |
| Thursday | November 19, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Tuesday | November 24, 2026 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
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- Winchester Youth Hockey Enrollment Process
- USA Hockey Neck Laceration Protection
- Family Enrollment Discounts
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