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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.02.2022 – Carrabec 3, Winthrop 2 |
| 9.07.2022 – Winthrop 1, Hall-Dale 0 |
| 9.12.2022 – Winthrop 4, Spruce Mountain/Dirigo 0 |
| 9.14.2022 – Mount Abram 6, Winthrop 0 |
| 9.16.2022 – Winthrop 2, Buckfield 1 |
| 9.20.2022 – Winthrop 8, Telstar 0 |
| 9.24.2022 – Monmouth Academy 2, Winthrop 0 |
| 9.27.2022 – Oak Hill 5, Winthrop 2 |
| 9.29.2022 – Winthrop 4, Mountain Valley 0 |
| 9.30.2022 – Winthrop 3, Lisbon 1 |
| 10.05.2022 – Oak Hill 7, Winthrop 2 |
| 10.07.2022 – Winthrop 2, Spruce Mountain/Dirigo 0 |
| 10.13.2022 – Winthrop 1, Buckfield 0 |
| 10.17.2022 – Hall-Dale 2, Winthrop 0 |
| 10.21.2022 – Oak Hill 4, Winthrop 3 |
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