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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.01.2023 – Oceanside 2, Medomak Valley 0 |
| 9.05.2023 – Medomak Valley 6, Maine Central Institute 0 |
| 9.08.2023 – Medomak Valley 9, Nokomis 0 |
| 9.12.2023 – Medomak Valley 1, Gardiner 0 |
| 9.14.2023 – Medomak Valley 5, Belfast 1 |
| 9.15.2023 – Medomak Valley 0, Lincoln Academy 0 |
| 9.21.2023 – Erskine Academy 1, Medomak Valley 0 |
| 9.23.2023 – Lincoln Academy 4, Medomak Valley 1 |
| 9.26.2023 – Medomak Valley 4, Waterville 2 |
| 9.28.2023 – Medomak Valley 1, Morse 0 |
| 10.03.2023 – Medomak Valley 2, Oceanside 0 |
| 10.10.2023 – Belfast 2, Medomak Valley 2 |
| 10.12.2023 – Morse 1, Medomak Valley 1 |
| 10.17.2023 – Medomak Valley 5, Erskine Academy 0 |
| 10.25.2023 – Medomak Valley 3, Gardiner 2 |
| 11.01.2023 – John Bapst 3, Medomak Valley 0 |
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