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| All Sports |
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| Basketball - Boys | | 12.09.2022 – Mount Abram 48, Winthrop 36 |
| 12.13.2022 – Winthrop 79, Wiscasset 13 |
| 12.19.2022 – Winthrop 80, Oak Hill 55 |
| 12.20.2022 – Winthrop 74, Telstar 21 |
| 12.22.2022 – Boothbay Region 54, Winthrop 45 |
| 12.28.2022 – Carrabec 49, Winthrop 42 |
| 12.30.2022 – Mountain Valley 58, Winthrop 45 |
| 1.03.2023 – Monmouth Academy 59, Winthrop 44 |
| 1.05.2023 – Spruce Mountain 70, Winthrop 31 |
| 1.07.2023 – Winthrop 56, Lisbon 49 |
| 1.13.2023 – Winthrop 63, Traip Academy 37 |
| 1.17.2023 – Winthrop 54, North Yarmouth Academy 42 |
| 1.21.2023 – Dirigo 72, Winthrop 54 |
| 1.24.2023 – Winthrop 66, Hall-Dale 59 |
| 1.27.2023 – Madison 52, Winthrop 51 |
| 1.31.2023 – Winthrop 75, Buckfield 32 |
| 2.03.2023 – Monmouth Academy 52, Winthrop 49 |
| 2.06.2023 – Lisbon 62, Winthrop 55 |
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