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| All Schools |
| All Sports |
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| Field Hockey | | 8.31.2022 – Dirigo 5, Winthrop 3 |
| 9.02.2022 – Winthrop 4, Lisbon 0 |
| 9.03.2022 – Winthrop 5, Oak Hill 1 |
| 9.09.2022 – Winthrop 8, Telstar 1 |
| 9.12.2022 – Winthrop 5, Hall-Dale 1 |
| 9.14.2022 – Winthrop 11, Boothbay Region 1 |
| 9.16.2022 – Winthrop 11, Mountain Valley 0 |
| 9.21.2022 – Spruce Mountain 4, Winthrop 3 |
| 9.26.2022 – Winthrop 5, Dirigo 0 |
| 9.28.2022 – Winthrop 4, Lisbon 1 |
| 9.30.2022 – Winthrop 7, Oak Hill 0 |
| 10.03.2022 – Winthrop 8, Telstar 0 |
| 10.12.2022 – Winthrop 4, Hall-Dale 0 |
| 10.17.2022 – Winthrop 6, Boothbay Region 0 |
| 10.27.2022 – Winthrop 5, Telstar 0 |
| 10.29.2022 – Winthrop 6, Oak Hill 0 |
| 11.02.2022 – Winthrop 1, Lisbon 0 |
| 11.05.2022 – Winthrop 2, Maine Central Institute 1 |
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