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| All Sports |
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| Field Hockey | | 9.08.2026 – Winthrop 10, Telstar 0 |
| 9.09.2026 – Winthrop 4, Oak Hill 0 |
| 9.11.2026 – Freeport 2, Winthrop 1 |
| 9.14.2026 – Winthrop 5, Dirigo 1 |
| 9.19.2026 – Winthrop 3, Spruce Mountain 2 |
| 9.23.2026 – Winthrop 2, Mountain Valley 1 |
| 9.25.2026 – Winthrop 3, Messalonskee 2 |
| 9.30.2026 – Winthrop 2, Boothbay Region 1 |
| 10.02.2026 – Winthrop 7, Dirigo 1 |
3:30 pm 10.02.2026 – Dirigo at Winthrop |
| 10.05.2026 – Winthrop 3, Hall-Dale/Monmouth 0 |
| 10.07.2026 – Winthrop 1, Spruce Mountain 0 |
| 10.09.2026 – Winthrop 4, Brunswick 0 |
4 pm 10.14.2026 – Winthrop at Oak Hill |
6 pm 10.16.2026 – Lisbon at Winthrop |
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