| All Schools |
| |
| Football |
| 9.01.2023 – South Portland 20, Cony 6 |
| 9.09.2023 – 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 |
| 10.06.2023 – Thornton Academy 14, South Portland 0 |
| 10.13.2023 – South Portland 27, Kennebunk 6 |
| 10.20.2023 – South Portland 7, Scarborough 0 |
| 10.31.2023 – Portland 34, South Portland 6 |
| |
| 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 |
| |
| Soccer - Girls |
| 8.31.2023 – South Portland 4, Biddeford 1 |
| 9.06.2023 – 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 |
| 10.02.2023 – South Portland 4, Westbrook 0 |
| 10.04.2023 – South Portland 3, Deering 0 |
| 10.09.2023 – Noble 1, South Portland 0 |
| 10.11.2023 – South Portland 3, Biddeford 0 |
| 10.13.2023 – Portland 1, South Portland 0 |
| 10.17.2023 – South Portland 4, Kennebunk 3 |
| 10.20.2023 – South Portland 3, Noble 0 |
| 10.24.2023 – Scarborough 5, South Portland 0 |
