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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.01.2023 – Erskine Academy 3, Winslow 2 |
| 9.06.2023 – Morse 2, Winslow 0 |
| 9.08.2023 – Winslow 1, Gardiner 1 |
| 9.12.2023 – Winslow 11, Lawrence 0 |
| 9.21.2023 – Winslow 7, Mount View 0 |
| 9.23.2023 – Winslow 8, Maine Central Institute 0 |
| 9.26.2023 – Winslow 8, Nokomis 2 |
| 9.30.2023 – Winslow 6, Waterville 1 |
| 10.09.2023 – Winslow 3, Maine Central Institute 0 |
| 10.10.2023 – Winslow 3, Leavitt 0 |
| 10.13.2023 – Winslow 3, Waterville 1 |
| 10.17.2023 – Winslow 11, Lawrence 0 |
| 10.25.2023 – Winslow 4, Caribou 2 |
| 11.02.2023 – Ellsworth 3, Winslow 2 |
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