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| All Sports |
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| Field Hockey | | 8.31.2023 – Oak Hill 3, Boothbay Region 2 |
| 9.06.2023 – Oak Hill 4, Telstar 0 |
| 9.08.2023 – Lewiston 2, Oak Hill 0 |
| 9.13.2023 – Oak Hill 2, Lisbon 2 |
| 9.20.2023 – Spruce Mountain 8, Oak Hill 0 |
| 9.22.2023 – Winthrop/Monmouth/Maranacook 6, Oak Hill 0 |
| 9.25.2023 – Hall-Dale 2, Oak Hill 0 |
| 9.28.2023 – Dirigo 1, Oak Hill 0 |
| 9.29.2023 – Oak Hill 2, Mountain Valley 1 |
| 10.02.2023 – Oak Hill 2, Boothbay Region 1 |
| 10.05.2023 – Oak Hill 0, Gray-New Gloucester/NYA 0 |
| 10.07.2023 – Oak Hill 2, Morse 1 |
| 10.11.2023 – Dirigo 5, Oak Hill 1 |
| 10.13.2023 – Lisbon 2, Oak Hill 1 |
| 10.24.2023 – Hall-Dale 2, Oak Hill 0 |
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