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| • Games for All Schools in September, 2023 |
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| Football |
| 9.1.2023 – South Portland 20, Cony 6 |
| 9.9.2023 – Lewiston 19, South Portland 16 |
| 9.15.2023 – Sanford 31, South Portland 20 |
| 9.22.2023 – South Portland 42, Gorham 18 |
| 9.29.2023 – Noble 28, South Portland 20 |
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| Soccer - Boys |
| 9.2.2023 – South Portland 0, Scarborough 0 |
| 9.5.2023 – South Portland 5, Thornton Academy 0 |
| 9.7.2023 – Falmouth 1, South Portland 0 |
| 9.12.2023 – South Portland 1, Bonny Eagle 1 |
| 9.19.2023 – Gorham 2, South Portland 1 |
| 9.21.2023 – South Portland 1, Deering 1 |
| 9.26.2023 – South Portland 4, Biddeford 2 |
| 9.28.2023 – South Portland 2, Marshwood 1 |
| 9.30.2023 – South Portland 8, Massabesic 0 |
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| Soccer - Girls |
| 9.6.2023 – South Portland 1, Cheverus 1 |
| 9.15.2023 – South Portland 2, Bonny Eagle 0 |
| 9.20.2023 – Gorham 2, South Portland 0 |
| 9.23.2023 – South Portland 5, Massabesic 0 |
| 9.27.2023 – Scarborough 3, South Portland 1 |
| 9.29.2023 – Thornton Academy 1, South Portland 1 |
| 9.30.2023 – Windham 2, South Portland 1 |
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