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| All Schools |
| All Sports |
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| Field Hockey | | 9.01.2021 – Mountain Valley 3, Oak Hill 0 |
| 9.03.2021 – Oak Hill 2, Spruce Mountain 1 |
| 9.08.2021 – Winthrop 8, Oak Hill 0 |
| 9.13.2021 – Lisbon 1, Oak Hill 0 |
| 9.17.2021 – Oak Hill 5, Telstar 1 |
| 9.27.2021 – Mountain Valley 2, Oak Hill 1 |
| 10.01.2021 – Winthrop 7, Oak Hill 0 |
| 10.04.2021 – Dirigo 4, Oak Hill 0 |
| 10.06.2021 – Oak Hill 1, Hall-Dale 0 |
3:30 PM 10.08.2021 – Oak Hill at Boothbay/Wiscasset |
| 10.14.2021 – Spruce Mountain 2, Oak Hill 1 |
| 10.15.2021 – Oak Hill 1, Boothbay/Wiscasset 0 |
| 10.26.2021 – Hall-Dale 1, Oak Hill 0 |
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