| All Schools |
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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 |
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| Football |
| 9.11.2021 – Foxcroft Academy 41, Oak Hill 20 |
| 9.18.2021 – Oak Hill 24, Lisbon/St. Dominic 13 |
| 9.25.2021 – Oak Hill 22, Madison/Carrabec/Valley 14 |
| 10.02.2021 – Oak Hill 25, Bucksport 20 |
| 10.08.2021 – Oak Hill 35, Poland Regional 20 |
6 PM 10.22.2021 – Oak Hill at Freeport |
6 PM 10.25.2021 – Oak Hill at Freeport |
1:30 PM 10.30.2021 – Hall-Dale/Winthrop/Maranacook at Oak Hill |
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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 |
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| Soccer - Girls |
| 9.30.2021 – Oak Hill 9, Carrabec 0 |
| 10.02.2021 – Oak Hill 8, Spruce Mountain 0 |
| 10.05.2021 – Oak Hill 3, Buckfield 0 |
3:30 PM 10.07.2021 – Oak Hill at Dirigo |
5:45 PM 10.08.2021 – Oak Hill at Winthrop/Monmouth |
3:30 PM 10.12.2021 – Telstar at Oak Hill |
| 10.13.2021 – Oak Hill 2, Mount Abram 0 |
6 PM 10.15.2021 – Oak Hill at Mountain Valley |
3:30 PM 10.16.2021 – Madison at Oak Hill |
| 10.18.2021 – Oak Hill 5, Madison 0 |
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