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| All Schools |
| All Sports |
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| Soccer - Boys | 6 pm 8.26.2026 – Gray-New Gloucester at Windham |
| 9.03.2026 – Deering 4, Windham 0 |
| 9.09.2026 – Falmouth 1, Windham 0 |
| 9.16.2026 – Windham 3, Bonny Eagle 2 |
| 9.18.2026 – Kennebunk 1, Windham 1 |
| 9.23.2026 – Portland 3, Windham 2 |
| 9.25.2026 – Windham 1, Cheverus 0 |
6 pm 9.28.2026 – Gorham at Windham |
| 9.30.2026 – Windham 2, Massabesic 0 |
| 10.03.2026 – Noble 1, Windham 1 |
| 10.05.2026 – Gorham 2, Windham 0 |
| 10.07.2026 – Sanford 2, Windham 0 |
| 10.09.2026 – Scarborough 3, Windham 0 |
| 10.14.2026 – Westbrook 5, Windham 1 |
| 10.17.2026 – Marshwood 1, Windham 0 |
| 10.20.2026 – Thornton Academy 2, Windham 0 |
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