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| All Schools |
| All Sports |
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| Field Hockey | | 8.31.2022 – Winslow 2, Maranacook 1 |
| 9.02.2022 – Gardiner 2, Winslow 0 |
| 9.07.2022 – Erskine Academy 3, Winslow 2 |
| 9.10.2022 – Maranacook 2, Winslow 1 |
| 9.13.2022 – Nokomis 5, Winslow 0 |
| 9.15.2022 – Cony 4, Winslow 1 |
| 9.17.2022 – Belfast 2, Winslow 1 |
| 9.20.2022 – Leavitt 3, Winslow 0 |
| 9.24.2022 – Winslow 3, Oceanside 2 |
| 9.27.2022 – Lawrence 7, Winslow 1 |
| 10.04.2022 – Maine Central Institute 3, Winslow 1 |
| 10.06.2022 – Nokomis 4, Winslow 1 |
| 10.13.2022 – Lawrence 6, Winslow 0 |
| 10.17.2022 – Messalonskee 6, Winslow 1 |
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