| • Games for All Schools in September, 2023 |
| |
| Football |
| 9.2.2023 – Freeport 39, Hall-Dale/Winthrop/Maranacook 33 |
| 9.9.2023 – 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 |
| |
| Soccer - Boys |
| 9.5.2023 – Freeport 7, North Yarmouth Academy 0 |
| 9.9.2023 – 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 |
| |
| Soccer - Girls |
| 9.5.2023 – Freeport 0, North Yarmouth Academy 0 |
| 9.12.2023 – Cape Elizabeth 2, Freeport 1 |
| 9.14.2023 – Freeport 0, Greely 0 |
| 9.15.2023 – Freeport 4, Traip Academy 0 |
| 9.19.2023 – York 0, Freeport 0 |
| 9.21.2023 – Freeport 2, Wells 0 |
| 9.23.2023 – Freeport 2, Waynflete 1 |
| 9.26.2023 – Yarmouth 1, Freeport 0 |
| 9.27.2023 – Freeport 2, Morse 0 |
| 9.29.2023 – Freeport 2, Lincoln Academy 1 |
| |
| Field Hockey |
| 9.1.2023 – Yarmouth 4, Freeport 3 |
| 9.5.2023 – Freeport 3, York 0 |
| 9.7.2023 – Freeport 3, Poland Regional 0 |
| 9.9.2023 – Freeport 5, Brunswick 0 |
| 9.15.2023 – Freeport 2, Lake Region 0 |
| 9.19.2023 – Freeport 6, Greely 1 |
| 9.23.2023 – Freeport 6, Poland Regional 0 |
| 9.28.2023 – York 2, Freeport 1 |
| 9.30.2023 – Freeport 2, Mount Ararat 2 |
