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| All Schools |
| All Sports |
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| Soccer - Boys | | 8.31.2023 – Freeport 2, Gray-New Gloucester 1 |
| 9.05.2023 – Freeport 7, North Yarmouth Academy 0 |
| 9.09.2023 – Freeport 2, Morse 2 |
| 9.12.2023 – Freeport 2, Cape Elizabeth 2 |
| 9.14.2023 – Greely 0, Freeport 0 |
| 9.19.2023 – York 2, Freeport 1 |
| 9.23.2023 – Freeport 2, Wells 0 |
| 9.26.2023 – Yarmouth 2, Freeport 1 |
| 9.29.2023 – Freeport 1, Lincoln Academy 0 |
| 9.30.2023 – Freeport 2, Traip Academy 1 |
| 10.03.2023 – Freeport 1, Waynflete 0 |
| 10.05.2023 – York 2, Freeport 1 |
| 10.10.2023 – Yarmouth 3, Freeport 1 |
| 10.12.2023 – Freeport 4, Cape Elizabeth 3 |
| 10.25.2023 – Lincoln Academy 3, Freeport 2 |
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