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| All Schools |
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| Soccer - Boys | | 9.03.2021 – Greater Portland 3, Pine Tree Academy 2 |
| 9.17.2021 – Rangeley 5, Greater Portland 0 |
| 9.21.2021 – Chop Point 2, Greater Portland 1 |
| 9.23.2021 – Valley 2, Greater Portland 1 |
| 9.28.2021 – Rangeley 4, Greater Portland 1 |
| 10.05.2021 – Vinalhaven 4, Greater Portland 0 |
| 10.07.2021 – Temple 5, Greater Portland 3 |
| 10.14.2021 – Pine Tree Academy 8, Greater Portland 0 |
| 10.15.2021 – Chop Point 2, Greater Portland 0 |
| 10.18.2021 – Chop Point 3, Greater Portland 1 |
| 10.22.2021 – Buckfield 7, Greater Portland 2 |
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| Soccer - Girls | | 9.03.2021 – Pine Tree Academy 8, Greater Portland 0 |
| 9.17.2021 – Rangeley 14, Greater Portland 0 |
| 9.23.2021 – Valley 10, Greater Portland 0 |
| 9.28.2021 – Rangeley 8, Greater Portland 0 |
| 10.05.2021 – Vinalhaven 5, Greater Portland 0 |
| 10.14.2021 – Pine Tree Academy 5, Greater Portland 0 |
1:30 PM 10.19.2021 – Greater Portland at Pine Tree Academy |
| 10.19.2021 – Pine Tree Academy 5, Greater Portland 0 |
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