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| All Sports |
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| Soccer - Boys | | 9.03.2026 – Winthrop 1, Oak Hill 1 |
| 9.10.2026 – Maranacook 1, Winthrop 0 |
| 9.12.2026 – Mountain Valley 3, Winthrop 2 |
| 9.14.2026 – Buckfield 6, Winthrop 1 |
| 9.16.2026 – Hall-Dale 5, Winthrop 0 |
| 9.18.2026 – Winthrop 4, Spruce Mountain 1 |
| 9.26.2026 – Winthrop 4, Mount Abram 3 |
| 9.29.2026 – Winthrop 3, Richmond 2 |
| 10.01.2026 – Leavitt 3, Winthrop 1 |
| 10.03.2026 – Lake Region 5, Winthrop 1 |
| 10.05.2026 – Lisbon 1, Winthrop 1 |
| 10.08.2026 – Cony 3, Winthrop 2 |
| 10.14.2026 – Monmouth Academy 7, Winthrop 0 |
| 10.17.2026 – Winthrop 1, Mountain Valley 0 |
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