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| All Schools |
| All Sports |
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| Football | | 9.01.2023 – Winslow 25, Old Town 7 |
| 9.09.2023 – Winslow 16, Madison 14 |
| 9.18.2023 – Nokomis 36, Winslow 14 |
| 9.23.2023 – Belfast 41, Winslow 35 |
| 9.29.2023 – Lisbon 20, Winslow 19 |
| 10.07.2023 – Winslow 18, Brewer 16 |
| 10.14.2023 – Oak Hill 25, Winslow 13 |
| 10.21.2023 – Foxcroft Academy 35, Winslow 14 |
| 10.31.2023 – Winslow 55, Maine Central Institute 14 |
| 11.04.2023 – Foxcroft Academy 62, Winslow 7 |
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