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| All Schools |
| All Sports |
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| Field Hockey | | 9.06.2024 – Winthrop 4, Hall-Dale/Monmouth 0 |
| 9.11.2024 – Winthrop 8, Mountain Valley 0 |
| 9.13.2024 – Winthrop 1, Messalonskee 0 |
| 9.16.2024 – Winthrop 8, Boothbay Region 0 |
| 9.18.2024 – Winthrop 9, Telstar 0 |
| 9.20.2024 – Winthrop 3, Dirigo 1 |
| 9.24.2024 – Winthrop 1, Lisbon 0 |
| 9.27.2024 – Winthrop 9, Oak Hill 0 |
| 9.30.2024 – Winthrop 4, Spruce Mountain 0 |
| 10.04.2024 – Winthrop 6, Winslow 1 |
| 10.11.2024 – Winthrop 3, Gardiner 2 |
| 10.16.2024 – Winthrop 5, Boothbay Region 1 |
| 10.18.2024 – Winthrop 13, Telstar 0 |
| 10.21.2024 – Spruce Mountain 3, Winthrop 1 |
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