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| All Schools |
| All Sports |
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| Football | | 9.06.2024 – Noble 28, Windham 14 |
| 9.13.2024 – Portland 29, Windham 7 |
7 pm 9.20.2024 – Thornton Academy at Windham |
| 9.21.2024 – Thornton Academy 54, Windham 14 |
| 9.27.2024 – South Portland 41, Windham 20 |
| 10.05.2024 – Windham 34, Bangor 18 |
| 10.11.2024 – Windham 20, Edward Little 14 |
| 10.18.2024 – Lewiston 34, Windham 29 |
| 10.25.2024 – Windham 17, Oxford Hills 14 |
| 11.01.2024 – Bonny Eagle 30, Windham 28 |
| 11.08.2024 – Portland 42, Windham 14 |
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