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| All Sports |
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| 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 |
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