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| All Schools |
| All Sports |
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| Football | 10 am 8.22.2026 – Windham at Kennebunk |
| 9.04.2026 – Oxford Hills/Buckfield 34, Windham 14 |
| 9.11.2026 – Windham 28, Sanford 7 |
| 9.18.2026 – Portland 39, Windham 13 |
| 9.25.2026 – Windham 21, Bangor 14 |
| 10.02.2026 – Bonny Eagle 42, Windham 6 |
| 10.09.2026 – Windham 34, Edward Little 9 |
| 10.16.2026 – Windham 35, Falmouth 21 |
| 10.23.2026 – Windham 41, Lewiston 6 |
| 10.30.2026 – Windham 19, Deering 0 |
| 11.06.2026 – Windham 21, Portland 14 |
TBA 11.13.2026 – Windham at Oxford Hills/Buckfield |
12 pm 11.14.2026 – Windham at Oxford Hills/Buckfield |
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