| All Schools |
| |
| Field Hockey |
| 9.04.2021 – Windham 6, South Portland 0 |
| 9.08.2021 – Thornton Academy 5, South Portland 0 |
| 9.10.2021 – Noble 4, South Portland 0 |
| 9.14.2021 – Gorham 11, South Portland 0 |
| 9.20.2021 – Massabesic 2, South Portland 0 |
| 9.28.2021 – Portland/Deering 2, South Portland 0 |
| 10.04.2021 – Biddeford 6, South Portland 0 |
| 10.06.2021 – Sanford 2, South Portland 0 |
| 10.08.2021 – Cheverus 11, South Portland 0 |
| 10.12.2021 – Westbrook 4, South Portland 0 |
| 10.14.2021 – Scarborough 9, South Portland 0 |
| 10.15.2021 – Marshwood 5, South Portland 0 |
| 10.18.2021 – Falmouth 7, South Portland 0 |
| |
| Football |
| 9.03.2021 – Scarborough 40, South Portland 3 |
| 9.10.2021 – South Portland 26, Massabesic 0 |
| 9.17.2021 – South Portland 59, Biddeford 34 |
| 10.01.2021 – Kennebunk 13, South Portland 12 |
| 10.08.2021 – South Portland 30, Noble 14 |
| 10.16.2021 – Portland 32, South Portland 7 |
7 PM 10.22.2021 – South Portland at Gorham |
| |
| 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 – South Portland 0, Falmouth 0 |
| 10.19.2021 – South Portland 4, Bonny Eagle 1 |
| |
| Soccer - Girls |
| 9.04.2021 – Cheverus 2, South Portland 0 |
| 9.07.2021 – Windham 3, South Portland 0 |
| 9.14.2021 – Thornton Academy 4, South Portland 2 |
| 9.16.2021 – Sanford 4, South Portland 1 |
| 9.18.2021 – Scarborough 6, South Portland 1 |
| 9.21.2021 – Noble 4, South Portland 0 |
| 9.23.2021 – Portland 4, South Portland 0 |
| 9.28.2021 – Marshwood 3, South Portland 1 |
| 9.30.2021 – South Portland 3, Massabesic 0 |
| 10.05.2021 – Gorham 3, South Portland 0 |
6 PM 10.07.2021 – South Portland at Kennebunk |
| 10.12.2021 – Deering 4, South Portland 0 |
| 10.14.2021 – Falmouth 3, South Portland 0 |
| 10.19.2021 – South Portland 1, Bonny Eagle 0 |
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