| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Thursday | September 7, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | Squirt 1 |
| Saturday | September 9, 2023 | 12:50 PM | 1:50 PM | Game | Hockeytown 4 | @ Micro Ice Squirt - AAA |
| Sunday | September 10, 2023 | 5:10 PM | 6:10 PM | Game | Kasabuski | @ Cape Ann Squirt - AAA |
| Tuesday | September 12, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | September 14, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | Squirt 1 |
| Saturday | September 16, 2023 | 11:40 AM | 12:40 PM | Game | Hockeytown 4 | @ Lynnfield-Saugus Squirt - AAA |
| Sunday | September 17, 2023 | 9:20 AM | 10:20 AM | Game | Cambridge | @ Brookline Squirt - AAA |
| Tuesday | September 19, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | September 21, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | Squirt 3 |
| Saturday | September 23, 2023 | 7:10 AM | 8:10 AM | Game | Hockeytown 3 | @ S&S Squirt - AAA |
| Sunday | September 24, 2023 | 7:10 AM | 8:10 AM | Game | Hockeytown 4 | @ Beverly Squirt - AAA |
| Tuesday | September 26, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3 |
| Thursday | September 28, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Sunday | October 1, 2023 | 7:10 AM | 8:10 AM | Game | Hockeytown 4 | @ Reading Squirt - AAA2 |
| Tuesday | October 3, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Thursday | October 5, 2023 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Saturday | October 7, 2023 | 11:40 AM | 12:40 PM | Game | Hockeytown 4 | @ S&S Squirt - AAA |
| Sunday | October 8, 2023 | 8:20 AM | 9:20 AM | Game | Hockeytown 4 | @ Reading Squirt - AAA2 |
| Tuesday | October 10, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Thursday | October 12, 2023 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3 |
| Saturday | October 14, 2023 | 6:40 PM | 7:40 PM | Game | Malden | @ Beverly Squirt - AAA |
| Sunday | October 15, 2023 | 10:20 AM | 11:20 AM | Game | Tewksbury 1 | @ Micro Ice Squirt - AAA |
| Tuesday | October 17, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3, Squirt 1 |
| Thursday | October 19, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | Squirt 1 |
| Saturday | October 21, 2023 | 10:30 AM | 11:30 AM | Game | Hockeytown 4 | @ North Reading Squirt - AAA |
| Sunday | October 22, 2023 | 3:20 PM | 4:20 PM | Game | Hockeytown 4 | @ Lynnfield-Saugus Squirt - AAA |
| Tuesday | October 24, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Thursday | October 26, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | Squirt 3 |
| Friday | October 27, 2023 | 5:40 PM | 6:40 PM | Game | Hockeytown 3 | @ Beverly Squirt - AAA |
| Tuesday | October 31, 2023 | 5:00 PM | 5:50 PM | Practice | LoConte | |
| Thursday | November 2, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Saturday | November 4, 2023 | 3:30 PM | 4:30 PM | Game | Revere | @ S&S Squirt - AAA |
| Tuesday | November 7, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Thursday | November 9, 2023 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 1 |
| Friday | November 10, 2023 | 12:40 PM | 1:40 PM | Game | Hockeytown 4 | @ Wakefield Squirt - AAA |
| Tuesday | November 14, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Thursday | November 16, 2023 | 6:00 PM | 6:50 PM | Practice | Flynn | Squirt 3 |
| Saturday | November 18, 2023 | 8:10 AM | 9:10 AM | Game | Kasabuski | @ Lynnfield-Saugus Squirt - AAA |
| Tuesday | November 21, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Saturday | November 25, 2023 | 8:30 AM | 9:30 AM | Game | Hockeytown 3 | @ Beverly Squirt - AAA |
| Tuesday | November 28, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | November 30, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Friday | December 1, 2023 | 6:10 PM | 7:10 PM | Game | Woburn | @ Reading Squirt - AAA2 |
| Sunday | December 3, 2023 | 5:00 PM | 6:00 PM | Game | Lynn | vs. Winthrop Squirt - AA |
| Tuesday | December 5, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3, Squirt 4 |
| Thursday | December 7, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3 |
| Tuesday | December 12, 2023 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | December 14, 2023 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Saturday | December 16, 2023 | 7:10 AM | 8:10 AM | Game | Chelmsford | @ Jr. Crusaders Squirt - AA |
| Tuesday | December 19, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 4 |
| Thursday | December 21, 2023 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Saturday | December 23, 2023 | 10:30 AM | 11:30 AM | Game | Hockeytown 4 | @ Allston-Brighton Squirt - AA |
| Tuesday | December 26, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Wednesday | December 27, 2023 | 12:20 PM | 1:20 PM | Game | Hockeytown 3 | @ So. Boston Squirt - AA |
| Thursday | December 28, 2023 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Sunday | December 31, 2023 | 7:10 AM | 8:10 AM | Game | Burlington | @ Medfield Squirt - AA |
| Tuesday | January 2, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3, Squirt 4 |
| Thursday | January 4, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3 |
| Saturday | January 6, 2024 | 3:20 PM | 4:20 PM | Game | Chelmsford | @ Jr. Crusaders Squirt - AA |
| Sunday | January 7, 2024 | 12:50 PM | 1:50 PM | Game | Framingham | @ Framingham Squirt - AA |
| Tuesday | January 9, 2024 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | January 11, 2024 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Saturday | January 13, 2024 | 8:10 AM | 9:10 AM | Game | Malden | @ Allston-Brighton Squirt - AA |
| Tuesday | January 16, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 4 |
| Thursday | January 18, 2024 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Sunday | January 21, 2024 | 8:10 AM | 9:10 AM | Game | Malden | vs. Winthrop Squirt - AA |
| Thursday | January 25, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Sunday | January 28, 2024 | 11:40 AM | 12:40 PM | Game | Malden | @ Allston-Brighton Squirt - AA |
| Thursday | February 1, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3 |
| Sunday | February 4, 2024 | 10:40 AM | 11:40 AM | Game | Burlington | @ Medfield Squirt - AA |
| Tuesday | February 6, 2024 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | February 8, 2024 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Sunday | February 11, 2024 | 8:10 AM | 9:10 AM | Game | Lynn | vs. Winthrop Squirt - AA |
| Tuesday | February 13, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 4 |
| Thursday | February 15, 2024 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Saturday | February 17, 2024 | 7:00 PM | 8:00 PM | Game | Hockeytown 3 | @ Jr. Crusaders Squirt - AA |
| Tuesday | February 20, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1, Squirt 3 |
| Thursday | February 22, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 1 |
| Saturday | February 24, 2024 | 8:10 AM | 9:10 AM | Game | Woburn | @ Waltham Squirt - AA1 |
| Sunday | February 25, 2024 | 4:10 PM | 5:10 PM | Game | Hockeytown 3 | vs. Winthrop Squirt - AA |
| Tuesday | February 27, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3, Squirt 4 |
| Thursday | February 29, 2024 | 7:00 PM | 7:50 PM | Practice | Flynn | Squirt 3 |
| Sunday | March 3, 2024 | 6:10 PM | 7:10 PM | Game | Charlestown | @ Framingham Squirt - AA |
| Tuesday | March 5, 2024 | 7:20 PM | 8:10 PM | Practice | Flynn Small | |
| Thursday | March 7, 2024 | 6:20 PM | 7:10 PM | Practice | Flynn Small | |
| Saturday | March 9, 2024 | 7:00 AM | 8:00 AM | Game | Woburn | @ Waltham Squirt - AA1 |
| Sunday | March 10, 2024 | 2:00 PM | 3:00 PM | Game | Woburn | @ Framingham Squirt - AA |
| Sunday | March 17, 2024 | 8:10 AM | 9:10 AM | Game | LoConte | @ Allston-Brighton Squirt - AA |
| Sunday | March 24, 2024 | 8:50 AM | 9:50 AM | Game | Cambridge | @ Waltham Squirt - AA1 |
| Saturday | March 30, 2024 | 4:40 PM | 5:40 PM | Game | Revere | vs. Winthrop Squirt 1 |
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- Placements FAQ's
- Parent's Guide to Buying Equipment
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- Winchester Youth Hockey Locker Room and Restroom Policy
- Winchester Youth Hockey Enrollment Process
- Holland Friday 3v3
- Note on 2024/2025 Tuition
- USA Hockey Neck Laceration Protection
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