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| All Schools |
| All Sports |
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| Football | | 9.07.2024 – Winslow 50, Maine Central Institute 6 |
| 9.13.2024 – Winslow 52, Madison 7 |
| 9.21.2024 – Foxcroft Academy 35, Winslow 3 |
| 9.28.2024 – Lisbon 26, Winslow 20 |
7 pm 10.04.2024 – Winslow at John Bapst |
| 10.07.2024 – John Bapst 35, Winslow 21 |
| 10.12.2024 – Wells 42, Winslow 6 |
| 10.19.2024 – Winslow 48, Belfast 6 |
| 10.25.2024 – Winslow 34, Old Town 6 |
TBA 11.01.2024 – Old Town at Winslow |
| 11.02.2024 – Winslow 44, Madison 18 |
| 11.09.2024 – Winslow 56, John Bapst 34 |
TBA 11.15.2024 – Winslow at Foxcroft Academy |
| 11.16.2024 – Foxcroft Academy 27, Winslow 7 |
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