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| All Sports |
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| Baseball | | 4.23.2025 – Winthrop 10, Boothbay Region 0 |
4 pm 4.25.2025 – Winthrop at Spruce Mountain |
4 pm 4.28.2025 – Maranacook at Winthrop |
4 pm 4.30.2025 – Oak Hill at Winthrop |
4 pm 5.01.2025 – Winthrop at Maranacook |
4 pm 5.02.2025 – Winthrop at Maranacook |
| 5.05.2025 – Winthrop 14, Madison 0 |
4 pm 5.07.2025 – Winthrop at Dirigo |
| 5.08.2025 – Dirigo 7, Winthrop 6 |
| 5.09.2025 – Old Orchard Beach 3, Winthrop 1 |
| 5.12.2025 – Mount View 6, Winthrop 3 |
| 5.14.2025 – Winthrop 8, Maine Central Institute 0 |
| 5.16.2025 – Monmouth Academy 4, Winthrop 2 |
4 pm 5.17.2025 – Winthrop at Monmouth Academy |
| 5.20.2025 – Winthrop 3, Mount Abram 0 |
4 pm 5.23.2025 – Mount Abram at Winthrop |
| 5.26.2025 – Lisbon 8, Winthrop 0 |
| 5.30.2025 – Winthrop 7, Lisbon 6 |
| 6.02.2025 – Winthrop 6, Mountain Valley 4 |
| 6.04.2025 – Winthrop 12, Hall-Dale 2 |
| 6.10.2025 – Dirigo 6, Winthrop 3 |
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