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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.03.2021 – South Portland 2, Cheverus 0 |
| 9.08.2021 – Windham 3, South Portland 0 |
| 9.14.2021 – South Portland 4, Thornton Academy 0 |
| 9.16.2021 – South Portland 6, Sanford 1 |
| 9.18.2021 – Scarborough 1, South Portland 0 |
| 9.21.2021 – Noble 0, South Portland 0 |
| 9.29.2021 – South Portland 0, Marshwood 0 |
| 10.02.2021 – South Portland 10, Massabesic 1 |
| 10.06.2021 – South Portland 2, Gorham 0 |
| 10.08.2021 – South Portland 4, Kennebunk 0 |
| 10.13.2021 – South Portland 2, Deering 0 |
| 10.16.2021 – Falmouth 0, South Portland 0 |
| 10.19.2021 – South Portland 4, Bonny Eagle 1 |
| 10.22.2021 – South Portland 5, Biddeford 0 |
| 10.27.2021 – South Portland 2, Bonny Eagle 0 |
| 10.29.2021 – Gorham 1, South Portland 0 |
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