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| All Schools |
| All Sports |
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| Football | | 9.02.2023 – Freeport 39, Hall-Dale/Winthrop/Maranacook 33 |
| 9.09.2023 – Freeport 28, Lisbon 16 |
| 9.18.2023 – John Bapst 27, Freeport 20 |
| 9.22.2023 – Poland Regional 22, Freeport 2 |
| 9.30.2023 – Oak Hill 24, Freeport 16 |
| 10.06.2023 – Oceanside 46, Freeport 0 |
| 10.13.2023 – Foxcroft Academy 56, Freeport 6 |
| 10.20.2023 – Cape Elizabeth 6, Freeport 3 |
| 10.31.2023 – Freeport 32, Poland Regional 14 |
| 11.04.2023 – Wells 42, Freeport 7 |
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