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| All Schools |
| All Sports |
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| 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 |
| 10.22.2021 – Portland 1, Cheverus 0 |
| 10.28.2021 – Windham 3, Portland 2 |
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