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| All Schools |
| All Sports |
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| Basketball - Girls | | 12.08.2023 – Maine Central Institute 50, Winslow 23 |
| 12.12.2023 – Belfast 60, Winslow 26 |
| 12.15.2023 – Lincoln Academy 71, Winslow 18 |
| 12.23.2023 – Medomak Valley 70, Winslow 11 |
| 12.28.2023 – Maine Central Institute 47, Winslow 21 |
| 1.02.2024 – Oceanside 94, Winslow 13 |
| 1.04.2024 – Leavitt 37, Winslow 34 |
| 1.06.2024 – Morse 49, Winslow 28 |
| 1.09.2024 – Mount View 66, Winslow 27 |
| 1.12.2024 – Winslow 45, Waterville 33 |
| 1.19.2024 – Lincoln Academy 67, Winslow 26 |
| 1.23.2024 – Erskine Academy 59, Winslow 21 |
6:30 pm 1.26.2024 – Waterville at Winslow |
6:30 pm 1.29.2024 – Erskine Academy at Winslow |
6:30 pm 1.30.2024 – Winslow at Leavitt |
6:30 pm 2.02.2024 – Belfast at Winslow |
6:30 pm 2.06.2024 – Winslow at Oceanside |
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