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| All Sports |
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| Soccer - Boys | | 9.05.2024 – Hall-Dale 6, Winthrop 2 |
| 9.10.2024 – Lisbon 3, Winthrop 3 |
| 9.17.2024 – Winthrop 2, Maranacook 1 |
| 9.19.2024 – Monmouth Academy 4, Winthrop 1 |
| 9.23.2024 – Mountain Valley 1, Winthrop 1 |
| 9.25.2024 – Mount Abram 3, Winthrop 0 |
| 9.27.2024 – Oak Hill 5, Winthrop 1 |
| 10.01.2024 – Winthrop 3, Lisbon 0 |
| 10.04.2024 – Winthrop 1, Buckfield 0 |
| 10.09.2024 – Monmouth Academy 5, Winthrop 1 |
| 10.10.2024 – Leavitt 1, Winthrop 1 |
| 10.16.2024 – Maranacook 2, Winthrop 1 |
| 10.19.2024 – Winthrop 1, Cony 0 |
| 10.21.2024 – Hall-Dale 3, Winthrop 1 |
| 10.30.2024 – Mount Abram 7, Winthrop 0 |
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