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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.10.2021 – Monmouth Academy 5, Winthrop 0 |
| 9.13.2021 – Winthrop 5, Spruce Mountain 2 |
| 9.17.2021 – Buckfield 2, Winthrop 1 |
| 9.25.2021 – Lisbon 11, Winthrop 1 |
| 9.28.2021 – Oak Hill 4, Winthrop 1 |
| 9.30.2021 – Winthrop 1, Mountain Valley 0 |
| 10.06.2021 – Oak Hill 6, Winthrop 3 |
| 10.08.2021 – Winthrop 3, Carrabec 2 |
6 PM 10.12.2021 – Winthrop at Mountain Valley |
| 10.14.2021 – Buckfield 3, Winthrop 1 |
| 10.22.2021 – Traip Academy 8, Winthrop 1 |
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