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| All Schools |
| All Sports |
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| Basketball - Girls | | 12.10.2022 – Presque Isle 62, Winslow 13 |
| 12.13.2022 – Maine Central Institute 61, Winslow 27 |
| 12.20.2022 – Lincoln Academy 55, Winslow 25 |
| 12.27.2022 – Oceanside 89, Winslow 6 |
| 12.29.2022 – Presque Isle 86, Winslow 8 |
| 1.03.2023 – Waterville 66, Winslow 32 |
| 1.07.2023 – Mount Desert Island 71, Winslow 28 |
| 1.10.2023 – Belfast 65, Winslow 23 |
| 1.13.2023 – Leavitt 80, Winslow 32 |
| 1.21.2023 – Mount Desert Island 71, Winslow 20 |
| 1.24.2023 – Lawrence 87, Winslow 12 |
| 1.27.2023 – Waterville 41, Winslow 12 |
| 1.30.2023 – Mount View 54, Winslow 18 |
| 1.31.2023 – Maine Central Institute 55, Winslow 20 |
| 2.03.2023 – Medomak Valley 76, Winslow 16 |
| 2.06.2023 – Belfast 58, Winslow 30 |
| 2.09.2023 – Maranacook 61, Winslow 27 |
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