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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.06.2023 – Winthrop 2, Lisbon 0 |
| 9.08.2023 – Cony 4, Winthrop 2 |
| 9.12.2023 – Winthrop 4, Maranacook 3 |
| 9.15.2023 – Monmouth Academy 5, Winthrop 0 |
| 9.20.2023 – Mount Abram 6, Winthrop 0 |
| 9.22.2023 – Oak Hill 7, Winthrop 0 |
| 9.27.2023 – Lisbon 2, Winthrop 0 |
| 9.30.2023 – Oak Hill 3, Winthrop 1 |
| 10.04.2023 – Monmouth Academy 7, Winthrop 1 |
| 10.05.2023 – Winthrop 1, Mountain Valley 0 |
| 10.06.2023 – Leavitt 7, Winthrop 0 |
| 10.11.2023 – Winthrop 1, Maranacook 0 |
| 10.16.2023 – Hall-Dale 7, Winthrop 1 |
| 10.25.2023 – Winthrop 1, Hall-Dale 0 |
| 10.31.2023 – Traip Academy 4, Winthrop 0 |
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