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| All Schools |
| All Sports |
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| Football | | 9.03.2021 – York 21, Winslow 7 |
| 9.10.2021 – Winslow 35, Hampden Academy 12 |
| 9.18.2021 – Winslow 44, Maine Central Institute 8 |
| 10.02.2021 – Wells 49, Winslow 13 |
| 10.09.2021 – Winslow 56, Oceanside 14 |
| 10.15.2021 – Winslow 35, Hermon 12 |
1 PM 10.23.2021 – Belfast at Winslow |
| 10.30.2021 – Winslow 30, Old Town 6 |
| 11.06.2021 – Winslow 64, Maine Central Institute 6 |
| 11.13.2021 – Winslow 38, Hermon 30 |
| 11.20.2021 – Cape Elizabeth 53, Winslow 8 |
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