| All Schools |
| |
| Soccer - Boys |
| 9.05.2023 – Pine Tree Academy 6, Temple 1 |
| 9.07.2023 – Pine Tree Academy 1, Valley 0 |
| 9.18.2023 – Buckfield 5, Pine Tree Academy 1 |
| 9.20.2023 – Pine Tree Academy 2, Rangeley 1 |
| 9.21.2023 – Pine Tree Academy 5, Chop Point 1 |
| 9.25.2023 – Buckfield 2, Pine Tree Academy 0 |
| 9.29.2023 – Pine Tree Academy 4, Telstar 0 |
| 10.03.2023 – Pine Tree Academy 4, Chop Point 2 |
| 10.04.2023 – Pine Tree Academy 7, Temple 2 |
| 10.05.2023 – Richmond 8, Pine Tree Academy 0 |
| 10.11.2023 – Islesboro 3, Pine Tree Academy 1 |
| 10.12.2023 – Pine Tree Academy 6, Telstar 0 |
| 10.16.2023 – Pine Tree Academy 7, Rangeley 0 |
| 10.17.2023 – Pine Tree Academy 8, Vinalhaven 0 |
| 10.24.2023 – Islesboro 2, Pine Tree Academy 1 |
| |
| Soccer - Girls |
| 9.05.2023 – Temple 5, Pine Tree Academy 1 |
| 9.07.2023 – Pine Tree Academy 2, Valley 0 |
| 9.08.2023 – Pine Tree Academy 3, Wiscasset 0 |
| 9.15.2023 – Pine Tree Academy 1, Lisbon 0 |
| 9.20.2023 – Pine Tree Academy 2, Rangeley 1 |
| 9.21.2023 – Pine Tree Academy 2, Lisbon 1 |
| 9.25.2023 – Pine Tree Academy 4, Dirigo 0 |
| 9.27.2023 – Pine Tree Academy 2, Wiscasset 0 |
| 10.04.2023 – Pine Tree Academy 1, Temple 0 |
| 10.10.2023 – Pine Tree Academy 1, Carrabec 0 |
| 10.11.2023 – Pine Tree Academy 2, Dirigo 0 |
| 10.14.2023 – Pine Tree Academy 3, Valley 0 |
| 10.16.2023 – Rangeley 1, Pine Tree Academy 0 |
| 10.17.2023 – Pine Tree Academy 2, Vinalhaven 1 |
| 10.24.2023 – Pine Tree Academy 3, Greenville 0 |
| 11.03.2023 – Rangeley 2, Pine Tree Academy 1 |
