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| All Schools |
| All Sports |
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| Soccer - Girls | | 8.31.2023 – Thornton Academy 3, Portland 1 |
| 9.06.2023 – Marshwood 6, Portland 1 |
| 9.09.2023 – Windham 6, Portland 0 |
| 9.13.2023 – Portland 4, Massabesic 0 |
| 9.15.2023 – Cheverus 4, Portland 0 |
| 9.22.2023 – Deering 1, Portland 0 |
| 9.26.2023 – Portland 5, Biddeford 3 |
| 9.29.2023 – Portland 2, Kennebunk 1 |
| 10.02.2023 – Scarborough 6, Portland 0 |
| 10.05.2023 – Portland 4, Gorham 4 |
| 10.06.2023 – Noble 4, Portland 2 |
| 10.10.2023 – Portland 5, Westbrook 1 |
| 10.13.2023 – Portland 1, South Portland 0 |
| 10.16.2023 – Sanford 2, Portland 1 |
| 10.20.2023 – Falmouth 2, Portland 0 |
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