| All Schools |
| |
| Field Hockey |
| 9.07.2019 – Freeport 4, Poland Regional 0 |
| 9.09.2019 – Freeport 1, Fryeburg Academy 1 |
| 9.11.2019 – Lake Region 1, Freeport 0 |
| 9.17.2019 – York 2, Freeport 1 |
| 9.19.2019 – Freeport 3, Fryeburg Academy 1 |
| 9.21.2019 – Freeport 4, Yarmouth 0 |
| 9.23.2019 – Freeport 7, Wells 2 |
| 9.25.2019 – York 2, Freeport 1 |
| 10.01.2019 – Freeport 4, Greely 1 |
| 10.03.2019 – Freeport 4, Cape Elizabeth 0 |
| 10.09.2019 – Freeport 0, Poland Regional 0 |
06:00 PM 10.16.2019 – Yarmouth at Freeport |
| |
| Football |
| 9.06.2019 – Freeport 41, Morse 13 |
| 9.20.2019 – Freeport 38, Lake Region 8 |
| 9.28.2019 – Freeport 14, Fryeburg Academy 7 |
| 10.04.2019 – Cape Elizabeth 21, Freeport 20 |
| 10.11.2019 – Freeport 2, Dirigo 0 |
06:00 PM 10.18.2019 – Poland Regional at Freeport |
01:30 PM 10.26.2019 – Freeport at Camden Hills |
| |
| Soccer - Boys |
| 9.05.2019 – Freeport 5, Gray-New Gloucester 0 |
| 9.10.2019 – Freeport 2, Greely 2 |
| 9.14.2019 – Freeport 3, Lake Region 0 |
| 9.17.2019 – Yarmouth 1, Freeport 0 |
| 9.20.2019 – York 1, Freeport 0 |
| 9.24.2019 – Freeport 2, Cape Elizabeth 1 |
| 9.26.2019 – Freeport 6, Wells 1 |
| 9.28.2019 – Freeport 2, Traip Academy 0 |
| 10.01.2019 – Freeport 5, Poland Regional 1 |
| 10.04.2019 – Greely 1, Freeport 1 |
| 10.08.2019 – Freeport 2, York 1 |
| 10.10.2019 – Freeport 1, Yarmouth 1 |
04:00 PM 10.15.2019 – Freeport at Fryeburg Academy |
03:30 PM 10.19.2019 – Cape Elizabeth at Freeport |
| |
| Soccer - Girls |
| 9.05.2019 – Freeport 2, Gray-New Gloucester 0 |
| 9.10.2019 – Freeport 6, Greely 2 |
| 9.13.2019 – Freeport 4, Lake Region 1 |
| 9.17.2019 – Freeport 1, Yarmouth 0 |
| 9.20.2019 – Freeport 2, York 0 |
| 9.24.2019 – Cape Elizabeth 1, Freeport 0 |
| 9.26.2019 – Freeport 6, Wells 0 |
| 9.28.2019 – Freeport 3, Saint Dominic 0 |
| 10.01.2019 – Freeport 7, Poland Regional 0 |
| 10.04.2019 – Freeport 2, Greely 2 |
| 10.08.2019 – Freeport 5, York 2 |
| 10.10.2019 – Yarmouth 1, Freeport 0 |
06:00 PM 10.15.2019 – Fryeburg Academy at Freeport |
01:30 PM 10.19.2019 – Cape Elizabeth at Freeport |
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