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| All Schools |
| All Sports |
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| Field Hockey | | 9.05.2024 – Cony 9, Winslow 0 |
| 9.07.2024 – Gardiner 7, Winslow 0 |
| 9.12.2024 – Belfast 7, Winslow 0 |
| 9.14.2024 – Dirigo 4, Winslow 0 |
| 9.18.2024 – Leavitt 4, Winslow 0 |
| 9.21.2024 – Maine Central Institute 2, Winslow 0 |
4 pm 9.24.2024 – Winslow at Lawrence |
| 9.26.2024 – Winslow 4, Morse 1 |
| 10.04.2024 – Maranacook/Winthrop 6, Winslow 1 |
| 10.04.2024 – Winthrop 6, Winslow 1 |
3:30 pm 10.07.2024 – Nokomis at Winslow |
| 10.08.2024 – Nokomis 2, Winslow 0 |
| 10.15.2024 – Winslow 5, Mount View 0 |
| 10.17.2024 – Winslow 2, Oceanside 0 |
3:30 pm 10.21.2024 – Erskine Academy at Winslow |
| 10.29.2024 – Dexter/Central 5, Winslow 0 |
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