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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.03.2021 – Hall-Dale 5, Oak Hill 2 |
| 9.08.2021 – Monmouth Academy 7, Oak Hill 3 |
| 9.13.2021 – Mount Abram 11, Oak Hill 0 |
| 9.17.2021 – Oak Hill 6, Dirigo 1 |
| 9.28.2021 – Oak Hill 4, Winthrop 1 |
| 10.02.2021 – Spruce Mountain 2, Oak Hill 0 |
| 10.04.2021 – Oak Hill 4, Carrabec 0 |
| 10.06.2021 – Oak Hill 6, Winthrop 3 |
| 10.08.2021 – Oak Hill 1, Buckfield 1 |
| 10.12.2021 – Monmouth Academy 4, Oak Hill 1 |
| 10.23.2021 – Sacopee Valley 4, Oak Hill 1 |
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