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| All Schools |
| All Sports |
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| Field Hockey | | 9.01.2021 – Winthrop 6, Dirigo 0 |
| 9.03.2021 – Winthrop 10, Lisbon 0 |
| 9.08.2021 – Winthrop 8, Oak Hill 0 |
| 9.10.2021 – Winthrop 14, Telstar 1 |
| 9.13.2021 – Winthrop 7, Hall-Dale 0 |
| 9.17.2021 – Winthrop 2, Mountain Valley 0 |
| 9.27.2021 – Winthrop 2, Dirigo 1 |
| 9.29.2021 – Winthrop 6, Lisbon 0 |
| 10.01.2021 – Winthrop 7, Oak Hill 0 |
| 10.04.2021 – Winthrop 7, Telstar 0 |
| 10.06.2021 – Winthrop 10, Boothbay/Wiscasset 0 |
| 10.13.2021 – Winthrop 4, Hall-Dale 0 |
| 10.27.2021 – Winthrop 4, Maranacook 0 |
| 10.30.2021 – Winthrop 3, Hall-Dale 0 |
| 11.03.2021 – Winthrop 8, Lisbon 1 |
| 11.06.2021 – Winthrop 3, Maine Central Institute 2 |
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