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| All Schools |
| All Sports |
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| Football | | 9.01.2023 – Portland 35, Thornton Academy 28 |
| 9.08.2023 – Portland 40, Edward Little 6 |
| 9.15.2023 – Portland 47, Lewiston 6 |
| 9.22.2023 – Portland 2, Falmouth 0 |
| 9.29.2023 – Portland 35, Windham 7 |
| 10.07.2023 – Portland 41, Noble 7 |
| 10.13.2023 – Portland 41, Scarborough 0 |
| 10.31.2023 – Portland 34, South Portland 6 |
| 11.06.2023 – Portland 32, Lewiston 6 |
| 11.11.2023 – Portland 29, Oxford Hills 22 |
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