| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Saturday | September 6, 2025 | 11:20 AM | 12:20 PM | Practice | Holland | |
| Sunday | September 7, 2025 | 9:20 AM | 10:20 AM | Game | West Roxbury | @ Parkway Peewee 1 |
| Tuesday | September 9, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | September 11, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 3 |
| Sunday | September 14, 2025 | 11:20 AM | 12:20 PM | Game | Dorchester | @ Westwood Peewee 1 |
| Tuesday | September 16, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Wednesday | September 17, 2025 | 7:10 PM | 8:00 PM | Practice | Burlington | Pee Wee 2, Pee Wee 3 |
| Thursday | September 18, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Sunday | September 21, 2025 | 2:00 PM | 3:00 PM | Game | Waltham | vs. Waltham Peewee 1 |
| Tuesday | September 23, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | September 25, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Sunday | September 28, 2025 | 10:10 AM | 11:10 AM | Game | Dorchester | @ Dorchester Peewee 1 |
| Tuesday | September 30, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | October 2, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Saturday | October 4, 2025 | 1:10 PM | 2:10 PM | Game | Somerville | @ Dedham Peewee 1 |
| Sunday | October 5, 2025 | 6:40 PM | 7:40 PM | Game | Malden | @ South Boston Peewee 1 |
| Tuesday | October 7, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Wednesday | October 8, 2025 | 7:10 PM | 8:00 PM | Practice | Burlington | Pee Wee 2, Pee Wee 3 |
| Thursday | October 9, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Friday | October 10, 2025 | 7:20 PM | 8:20 PM | Game | Woburn | vs. Lexington/Bedford Peewee 1 |
| Sunday | October 12, 2025 | 9:20 AM | 10:20 AM | Game | Framingham | vs. Framingham Peewee 1 |
| Tuesday | October 14, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | October 16, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Sunday | October 19, 2025 | 11:40 AM | 12:40 PM | Game | Wellesley Rink 1 | vs. Wellesley Peewee 1 |
| Tuesday | October 21, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Wednesday | October 22, 2025 | 7:10 PM | 8:00 PM | Practice | Burlington | Pee Wee 2, Pee Wee 3 |
| Thursday | October 23, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Sunday | October 26, 2025 | 12:30 PM | 1:30 PM | Game | Dorchester | @ Dorchester Peewee 1 |
| Tuesday | October 28, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | October 30, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Sunday | November 2, 2025 | 10:30 AM | 11:30 AM | Game | Malden | vs. Natick Peewee 1 |
| Tuesday | November 4, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Wednesday | November 5, 2025 | 7:10 PM | 8:00 PM | Practice | Burlington | Pee Wee 2, Pee Wee 3 |
| Thursday | November 6, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Saturday | November 8, 2025 | 3:00 PM | 4:00 PM | Game | Cambridge | vs. Cambridge Peewee 1 |
| Tuesday | November 11, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | November 13, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Tuesday | November 18, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Thursday | November 20, 2025 | 8:00 PM | 8:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Tuesday | November 25, 2025 | 7:00 PM | 7:50 PM | Practice | Flynn | Pee Wee 2, Pee Wee 3 |
| Wednesday | November 26, 2025 | 7:10 PM | 8:00 PM | Practice | Burlington | Pee Wee 2, Pee Wee 3 |
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- USA Hockey Zero Tolerance Policy
- 2025 Placements Schedule
- How to Register
- Placements FAQ's
- Parent's Guide to Buying Equipment
- Massachusetts Hockey Tournament Page
- Winchester Youth Hockey Locker Room and Restroom Policy
- Winchester Youth Hockey Enrollment Process
- Holland Friday 3v3
- Note on 2025/2026 Tuition
- USA Hockey Neck Laceration Protection
- Goalie Skills
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- Registration