| All Schools |
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| Field Hockey |
| 9.01.2021 – York 4, Freeport 0 |
| 9.06.2021 – Yarmouth 2, Freeport 1 |
| 9.11.2021 – Cape Elizabeth 5, Freeport 0 |
| 9.15.2021 – Freeport 4, Greely 2 |
| 9.21.2021 – Freeport 2, Poland Regional 1 |
| 9.27.2021 – Freeport 2, Lake Region 0 |
| 10.02.2021 – Cape Elizabeth 3, Freeport 2 |
| 10.05.2021 – Freeport 2, Greely 1 |
| 10.07.2021 – Yarmouth 2, Freeport 1 |
| 10.11.2021 – Freeport 5, Gray-New Gloucester 1 |
| 10.13.2021 – Freeport 3, Fryeburg Academy 2 |
| 10.16.2021 – Freeport 1, Lake Region 0 |
| |
| Football |
| 9.04.2021 – Freeport 33, Carrabec/Madison Co-op 0 |
| 9.11.2021 – Freeport 46, John Bapst 12 |
| 9.17.2021 – Foxcroft Academy 28, Freeport 12 |
| 9.25.2021 – Freeport 27, Lisbon/St. Dominic 13 |
| 10.08.2021 – Freeport 26, Bucksport 7 |
7 PM 10.15.2021 – Freeport at Hall-Dale/Winthrop/Maranacook |
| 10.18.2021 – Hall-Dale/Winthrop/Maranacook 40, Freeport 14 |
6 PM 10.22.2021 – Oak Hill at Freeport |
6 PM 10.25.2021 – Oak Hill at Freeport |
| |
| 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 |
6 PM 10.14.2021 – Freeport at Poland Regional |
| 10.19.2021 – Freeport 1, Cape Elizabeth 0 |
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| Soccer - Girls |
| 9.04.2021 – York 2, Freeport 1 |
| 9.07.2021 – Yarmouth 5, Freeport 2 |
| 9.14.2021 – Freeport 7, Lake Region 0 |
| 9.17.2021 – Cape Elizabeth 2, Freeport 0 |
| 10.02.2021 – Freeport 2, Wells 0 |
| 10.05.2021 – York 3, Freeport 0 |
| 10.07.2021 – Yarmouth 3, Freeport 2 |
6 PM 10.08.2021 – Freeport at Yarmouth |
| 10.12.2021 – Freeport 2, Greely 1 |
6 PM 10.15.2021 – Freeport at Poland Regional |
7 PM 10.19.2021 – Freeport at Cape Elizabeth |
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