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| All Schools |
| All Sports |
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| Football | | 9.04.2021 – Cony 36, Skowhegan 35 |
| 9.10.2021 – Lawrence 27, Skowhegan 20 |
| 9.17.2021 – Oxford Hills 27, Skowhegan 13 |
| 9.24.2021 – Skowhegan 60, Falmouth/Greely 0 |
| 10.01.2021 – Skowhegan 61, Brunswick 14 |
| 10.08.2021 – Skowhegan 40, Brewer 8 |
| 10.15.2021 – Windham 21, Skowhegan 7 |
| 10.22.2021 – Skowhegan 42, Mount Blue 0 |
| 10.29.2021 – Skowhegan 42, Falmouth/Greely 0 |
| 11.05.2021 – Windham 7, Skowhegan 6 |
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