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| All Schools |
| All Sports |
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| Football | 10 am 8.23.2025 – Mountain Valley at Winslow |
1 pm 8.30.2025 – Oak Hill at Winslow |
| 9.06.2025 – Winslow 54, Maranacook 0 |
| 9.12.2025 – Winslow 63, Belfast 22 |
1 pm 9.13.2025 – Belfast at Winslow |
| 9.20.2025 – Winslow 47, Freeport 7 |
| 9.27.2025 – John Bapst/Bangor Christian/Ce 27, Winslow 14 |
| 10.03.2025 – Winslow 38, Mattanawcook/Lee/Penobscot 0 |
| 10.11.2025 – Winslow 63, Maine Central Institute 12 |
| 10.17.2025 – Winslow 56, Madison/Carrabec/Valley 15 |
| 10.25.2025 – Winslow 56, Morse 14 |
1 pm 11.08.2025 – Madison at Winslow |
| 11.08.2025 – Winslow 68, Madison/Carrabec/Valley 7 |
| 11.15.2025 – Winslow 42, John Bapst/Bangor Christian/Ce 14 |
| 11.22.2025 – Winthrop/Monmouth/HDMS 41, Winslow 14 |
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