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| All Schools |
| All Sports |
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| 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 |
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