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| All Schools |
| All Sports |
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| Field Hockey | | 9.03.2026 – Marshwood 4, South Portland/Westbrook 1 |
| 9.09.2026 – Kennebunk 12, South Portland/Westbrook 1 |
| 9.09.2026 – Kennebunk/Sanford 12, South Portland/Westbrook 1 |
| 9.11.2026 – Falmouth 8, South Portland/Westbrook 0 |
| 9.15.2026 – Scarborough 5, South Portland/Westbrook 1 |
| 9.17.2026 – Noble 2, South Portland/Westbrook 0 |
| 9.21.2026 – Cheverus 10, South Portland/Westbrook 0 |
| 9.23.2026 – South Portland/Westbrook 6, Portland/Deering 1 |
| 9.25.2026 – Massabesic 4, South Portland/Westbrook 3 |
| 9.29.2026 – Bonny Eagle 2, South Portland/Westbrook 0 |
| 10.01.2026 – Thornton Academy 12, South Portland/Westbrook 0 |
| 10.05.2026 – Windham 5, South Portland/Westbrook 0 |
| 10.09.2026 – Biddeford 9, South Portland/Westbrook 0 |
4 pm 10.13.2026 – Scarborough at South Portland/Westbrook |
4 pm 10.19.2026 – Gorham at South Portland/Westbrook |
4 pm 10.20.2026 – Scarborough at South Portland/Westbrook |
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