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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.02.2023 – South Portland 0, Scarborough 0 |
| 9.05.2023 – South Portland 5, Thornton Academy 0 |
| 9.07.2023 – 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 |
| 10.03.2023 – South Portland 3, Kennebunk 1 |
| 10.05.2023 – South Portland 7, Noble 1 |
| 10.10.2023 – Windham 3, South Portland 1 |
| 10.12.2023 – Scarborough 5, South Portland 1 |
| 10.17.2023 – Westbrook 3, South Portland 1 |
| 10.20.2023 – South Portland 1, Bonny Eagle 0 |
| 10.25.2023 – Windham 4, South Portland 0 |
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