| All Schools |
| |
| Football |
| 9.10.2021 – Portland 40, Deering 0 |
| 10.01.2021 – Portland 28, Marshwood 14 |
| 10.08.2021 – Portland 55, Biddeford 8 |
| 10.16.2021 – Portland 32, South Portland 7 |
7 PM 10.22.2021 – Lewiston at Portland |
| |
| Soccer - Boys |
| 9.02.2021 – Portland 1, Gorham 0 |
| 9.08.2021 – Cheverus 2, Portland 1 |
| 9.11.2021 – Windham 2, Portland 0 |
| 9.14.2021 – Portland 4, Biddeford 1 |
| 9.16.2021 – Portland 3, Thornton Academy 0 |
| 9.18.2021 – Portland 7, Westbrook 0 |
| 9.22.2021 – Scarborough 2, Portland 1 |
| 10.02.2021 – Portland 3, Sanford 0 |
| 10.05.2021 – Portland 12, Massabesic 0 |
| 10.09.2021 – Portland 9, Noble 0 |
| 10.13.2021 – Portland 4, Kennebunk 0 |
| 10.16.2021 – Marshwood 4, Portland 1 |
| 10.19.2021 – Portland 3, Falmouth 1 |
| |
| Soccer - Girls |
| 9.02.2021 – Gorham 6, Portland 0 |
| 9.09.2021 – Windham 5, Portland 1 |
| 9.14.2021 – Portland 3, Biddeford 1 |
| 9.16.2021 – Thornton Academy 2, Portland 1 |
| 9.18.2021 – Portland 7, Westbrook 1 |
| 9.21.2021 – Scarborough 5, Portland 0 |
| 9.23.2021 – Portland 4, South Portland 0 |
| 10.05.2021 – Portland 7, Massabesic 1 |
| 10.07.2021 – Noble 4, Portland 1 |
| 10.12.2021 – Portland 2, Kennebunk 1 |
| 10.15.2021 – Marshwood 0, Portland 0 |
| 10.19.2021 – Falmouth 1, Portland 0 |
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