| All Schools |
| |
| Field Hockey |
| 9.06.2019 – Windham 3, South Portland 0 |
| 9.09.2019 – Kennebunk 3, South Portland 1 |
| 9.10.2019 – Thornton Academy 2, South Portland 1 |
| 9.12.2019 – South Portland 2, Noble 0 |
| 9.16.2019 – Gorham 5, South Portland 1 |
| 9.18.2019 – South Portland 4, Westbrook 0 |
| 9.21.2019 – Massabesic 6, South Portland 1 |
| 9.24.2019 – Falmouth 2, South Portland 1 |
| 9.26.2019 – South Portland 1, Marshwood 0 |
| 9.30.2019 – South Portland 5, Portland/Deering 1 |
| 10.04.2019 – Biddeford 5, South Portland 1 |
| 10.08.2019 – Sanford 4, South Portland 0 |
| 10.10.2019 – Cheverus 2, South Portland 1 |
06:00 PM 10.16.2019 – South Portland at Scarborough |
| |
| Football |
| 9.06.2019 – Deering 30, South Portland 14 |
| 9.14.2019 – South Portland 19, Cheverus 14 |
| 9.20.2019 – South Portland 49, Noble 7 |
| 9.27.2019 – Massabesic 26, South Portland 14 |
| 10.04.2019 – South Portland 31, Gorham 28 |
| 10.11.2019 – South Portland 35, Portland 7 |
06:00 PM 10.18.2019 – South Portland at Westbrook/Waynflete |
06:00 PM 10.25.2019 – Sanford at South Portland |
| |
| Soccer - Boys |
| 9.05.2019 – Cheverus 0, South Portland 0 |
| 9.10.2019 – South Portland 3, Windham 1 |
| 9.17.2019 – South Portland 1, Thornton Academy 0 |
| 9.19.2019 – South Portland 2, Sanford 0 |
| 9.21.2019 – Scarborough 2, South Portland 0 |
| 9.24.2019 – South Portland 2, Noble 1 |
| 9.26.2019 – South Portland 4, Portland 2 |
| 10.01.2019 – South Portland 2, Marshwood 1 |
| 10.04.2019 – South Portland 6, Massabesic 0 |
| 10.08.2019 – Gorham 4, South Portland 0 |
| 10.11.2019 – Kennebunk 2, South Portland 0 |
05:00 PM 10.15.2019 – South Portland at Deering |
06:00 PM 10.18.2019 – Falmouth at South Portland |
06:00 PM 10.22.2019 – South Portland at Bonny Eagle |
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| Soccer - Girls |
| 9.06.2019 – Cheverus 5, South Portland 1 |
| 9.10.2019 – Windham 3, South Portland 0 |
| 9.17.2019 – Thornton Academy 2, South Portland 1 |
| 9.19.2019 – South Portland 4, Sanford 3 |
| 9.21.2019 – Scarborough 3, South Portland 0 |
| 9.24.2019 – Noble 2, South Portland 0 |
| 9.27.2019 – Portland 2, South Portland 0 |
| 10.01.2019 – Marshwood 4, South Portland 2 |
| 10.04.2019 – South Portland 4, Massabesic 1 |
| 10.08.2019 – Gorham 4, South Portland 0 |
| 10.10.2019 – Kennebunk 5, South Portland 4 |
06:00 PM 10.15.2019 – Deering at South Portland |
06:30 PM 10.18.2019 – South Portland at Falmouth |
06:00 PM 10.22.2019 – Bonny Eagle at South Portland |
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