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| • Games for All Schools in September, 2023 |
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| Football |
| 9.1.2023 – Portland 35, Thornton Academy 28 |
| 9.8.2023 – Portland 40, Edward Little 6 |
| 9.15.2023 – Portland 47, Lewiston 6 |
| 9.22.2023 – Portland 2, Falmouth 0 |
| 9.29.2023 – Portland 35, Windham 7 |
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| Soccer - Boys |
| 9.1.2023 – Portland 1, Gorham 1 |
| 9.5.2023 – Portland 3, Marshwood 0 |
| 9.7.2023 – Portland 4, Noble 0 |
| 9.12.2023 – Portland 2, Falmouth 0 |
| 9.14.2023 – Portland 4, Sanford 0 |
| 9.19.2023 – Portland 6, Thornton Academy 0 |
| 9.21.2023 – Portland 5, Westbrook 0 |
| 9.26.2023 – Portland 3, Scarborough 0 |
| 9.30.2023 – Kennebunk 1, Portland 0 |
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| Soccer - Girls |
| 9.6.2023 – Marshwood 6, Portland 1 |
| 9.9.2023 – 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 |
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