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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.07.2021 – Yarmouth 3, Freeport 0 |
| 9.17.2021 – Cape Elizabeth 1, Freeport 0 |
| 9.23.2021 – Freeport 1, Gray-New Gloucester 0 |
| 9.27.2021 – Yarmouth 0, Freeport 0 |
| 10.05.2021 – York 2, Freeport 1 |
| 10.08.2021 – Freeport 3, Wells 0 |
| 10.12.2021 – Greely 2, Freeport 0 |
| 10.14.2021 – Freeport 4, Poland Regional 0 |
| 10.19.2021 – Freeport 1, Cape Elizabeth 0 |
| 10.22.2021 – Freeport 7, Lake Region 3 |
| 10.27.2021 – Freeport 2, Greely 1 |
| 10.30.2021 – Yarmouth 2, Freeport 1 |
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