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| All Schools |
| All Sports |
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| Football | | 9.04.2021 – Windham 47, Brunswick 8 |
| 9.17.2021 – Windham 27, Lawrence 6 |
| 9.25.2021 – Windham 51, Brewer 0 |
| 10.01.2021 – Windham 43, Messalonskee 12 |
7 PM 10.08.2021 – Windham at Cony |
| 10.09.2021 – Windham 36, Cony 7 |
| 10.15.2021 – Windham 21, Skowhegan 7 |
7 PM 10.22.2021 – Windham at Sanford |
| 10.29.2021 – Windham 56, Mount Blue 0 |
| 11.05.2021 – Windham 7, Skowhegan 6 |
7 PM 11.12.2021 – Lawrence at Windham |
| 11.13.2021 – Windham 42, Lawrence 35 |
| 11.20.2021 – Marshwood 14, Windham 13 |
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