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| All Schools |
| All Sports |
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| Field Hockey | | 9.01.2021 – York 4, Freeport 0 |
| 9.06.2021 – Yarmouth 2, Freeport 1 |
| 9.11.2021 – Cape Elizabeth 5, Freeport 0 |
| 9.15.2021 – Freeport 4, Greely 2 |
| 9.21.2021 – Freeport 2, Poland Regional 1 |
| 9.27.2021 – Freeport 2, Lake Region 0 |
| 10.02.2021 – Cape Elizabeth 3, Freeport 2 |
| 10.05.2021 – Freeport 2, Greely 1 |
| 10.07.2021 – Yarmouth 2, Freeport 1 |
| 10.11.2021 – Freeport 5, Gray-New Gloucester 1 |
| 10.13.2021 – Freeport 3, Fryeburg Academy 2 |
| 10.16.2021 – Freeport 1, Lake Region 0 |
| 10.21.2021 – Freeport 6, Gray-New Gloucester 0 |
| 10.27.2021 – Yarmouth 2, Freeport 1 |
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