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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.05.2023 – Oak Hill 0, Monmouth Academy 0 |
| 9.12.2023 – Mount Abram 5, Oak Hill 1 |
| 9.14.2023 – Hall-Dale 4, Oak Hill 2 |
| 9.20.2023 – Oak Hill 4, Mountain Valley 0 |
| 9.22.2023 – Oak Hill 7, Winthrop 0 |
| 9.27.2023 – Monmouth Academy 4, Oak Hill 2 |
| 9.30.2023 – Oak Hill 3, Winthrop 1 |
| 10.04.2023 – Hall-Dale 1, Oak Hill 0 |
| 10.06.2023 – Poland Regional 3, Oak Hill 2 |
| 10.10.2023 – Oak Hill 1, Maranacook 0 |
| 10.11.2023 – Oak Hill 3, Mountain Valley 0 |
| 10.13.2023 – Traip Academy 3, Oak Hill 2 |
| 10.16.2023 – Oak Hill 1, Lisbon 0 |
| 10.20.2023 – Morse 4, Oak Hill 1 |
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