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| All Schools |
| All Sports |
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| Soccer - Boys | 4:30 pm 8.27.2026 – Pine Tree Academy at Richmond |
| 9.03.2026 – Pine Tree Academy 6, Dirigo 0 |
| 9.08.2026 – Pine Tree Academy 6, Carrabec/Madison Co-op 1 |
| 9.10.2026 – Pine Tree Academy 8, Islesboro 0 |
| 9.11.2026 – Pine Tree Academy 4, Boothbay/Wiscasset 1 |
| 9.22.2026 – Pine Tree Academy 8, Temple 0 |
| 9.29.2026 – Pine Tree Academy 6, Boothbay/Wiscasset 0 |
| 10.01.2026 – Pine Tree Academy 5, Vinalhaven/North Haven 0 |
| 10.06.2026 – Pine Tree Academy 8, Rangeley 0 |
| 10.09.2026 – Pine Tree Academy 8, Carrabec/Madison Co-op 0 |
2:30 pm 10.13.2026 – Pine Tree Academy at Greenville |
| 10.15.2026 – Pine Tree Academy 1, Telstar 0 |
| 10.19.2026 – Pine Tree Academy 6, Valley 0 |
| 10.20.2026 – Pine Tree Academy 6, Greenville 0 |
4 pm 10.22.2026 – Richmond at Pine Tree Academy |
| 10.27.2026 – Pine Tree Academy 5, Rangeley 0 |
3 pm 10.30.2026 – Temple at Pine Tree Academy |
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