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| All Schools |
| All Sports |
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| Football | | 9.03.2022 – Winslow 58, Old Town 14 |
| 9.10.2022 – Medomak Valley 40, Winslow 0 |
| 9.17.2022 – Winslow 28, Belfast 27 |
| 9.23.2022 – Winslow 28, Mount Blue 18 |
| 9.30.2022 – Hall-Dale/Winthrop/Maranacook 35, Winslow 7 |
| 10.08.2022 – Cheverus 28, Winslow 13 |
| 10.15.2022 – Hermon 37, Winslow 7 |
| 10.22.2022 – Maine Central Institute 28, Winslow 14 |
| 10.29.2022 – Winslow 27, Nokomis 12 |
| 11.05.2022 – Medomak Valley 21, Winslow 13 |
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