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| All Schools |
| All Sports |
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| Basketball - Girls | | 12.09.2022 – Winthrop 66, Mount Abram 27 |
| 12.12.2022 – Winthrop 74, Wiscasset 16 |
| 12.14.2022 – Winthrop 65, Telstar 29 |
| 12.19.2022 – Winthrop 66, Oak Hill 17 |
| 12.26.2022 – Winthrop 56, Boothbay Region 20 |
| 12.28.2022 – Carrabec 38, Winthrop 29 |
| 12.30.2022 – Winthrop 59, Mountain Valley 37 |
| 1.02.2023 – Winthrop 49, Monmouth Academy 39 |
| 1.04.2023 – Spruce Mountain 56, Winthrop 31 |
| 1.07.2023 – Kents Hill 61, Winthrop 55 |
| 1.13.2023 – Winthrop 48, Traip Academy 45 |
| 1.17.2023 – North Yarmouth Academy 79, Winthrop 31 |
| 1.21.2023 – Winthrop 55, Dirigo 31 |
| 1.28.2023 – Hall-Dale 69, Winthrop 44 |
| 1.30.2023 – Winthrop 60, Buckfield 20 |
| 1.31.2023 – Winthrop 65, Madison 55 |
| 2.03.2023 – Monmouth Academy 39, Winthrop 34 |
| 2.06.2023 – Winthrop 58, Kents Hill 43 |
| 2.14.2023 – Winthrop 44, Traip Academy 41 |
| 2.21.2023 – Old Orchard Beach 53, Winthrop 28 |
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