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| All Schools |
| All Sports |
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| Football | | 9.01.2023 – Windham 35, Skowhegan 0 |
| 9.09.2023 – Windham 35, Bangor 6 |
| 9.15.2023 – Windham 48, Edward Little 0 |
| 9.22.2023 – Thornton Academy 37, Windham 6 |
| 9.29.2023 – Portland 35, Windham 7 |
| 10.06.2023 – Windham 21, Scarborough 3 |
| 10.13.2023 – Oxford Hills 35, Windham 14 |
| 10.20.2023 – Windham 33, Lewiston 0 |
| 10.31.2023 – Bonny Eagle 35, Windham 21 |
| 11.06.2023 – Oxford Hills 6, Windham 0 |
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