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| All Schools |
| All Sports |
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| Football | | 8.28.2026 – Bangor 20, South Portland 14 |
| 9.04.2026 – Bonny Eagle 21, South Portland 14 |
| 9.11.2026 – Thornton Academy 35, South Portland 21 |
| 9.18.2026 – South Portland 20, Scarborough 13 |
| 9.25.2026 – South Portland 27, Cheverus/Waynflete 20 |
| 10.02.2026 – South Portland 40, Sanford 0 |
| 10.09.2026 – South Portland 21, Massabesic 18 |
| 10.16.2026 – Noble 21, South Portland 7 |
| 10.23.2026 – Winnacunnet 34, South Portland 14 |
| 10.30.2026 – Portland 27, South Portland 7 |
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