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| All Schools |
| All Sports |
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| Field Hockey | | 9.01.2021 – Fryeburg Academy 5, Poland Regional 1 |
| 9.03.2021 – Fryeburg Academy 3, Gray-New Gloucester 0 |
| 9.11.2021 – Lake Region 1, Fryeburg Academy 0 |
| 9.21.2021 – Fryeburg Academy 5, Greely 3 |
| 9.23.2021 – York 4, Fryeburg Academy 1 |
| 9.27.2021 – Cape Elizabeth 5, Fryeburg Academy 4 |
| 9.29.2021 – Fryeburg Academy 2, Poland Regional 1 |
| 10.01.2021 – Fryeburg Academy 2, Yarmouth 1 |
| 10.04.2021 – York 3, Fryeburg Academy 0 |
| 10.07.2021 – Fryeburg Academy 4, Lake Region 1 |
| 10.11.2021 – Fryeburg Academy 3, Yarmouth 1 |
| 10.13.2021 – Freeport 3, Fryeburg Academy 2 |
| 10.21.2021 – Fryeburg Academy 5, Poland Regional 0 |
| 10.28.2021 – Leavitt 3, Fryeburg Academy 2 |
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