| All Schools |
| |
| Field Hockey |
| 9.01.2021 – Winslow 10, Waterville 0 |
| 9.03.2021 – Winslow 2, Gardiner 1 |
| 9.08.2021 – Winslow 9, Erskine Academy 0 |
| 9.28.2021 – Lawrence 5, Winslow 0 |
| 10.01.2021 – Cony 7, Winslow 0 |
| 10.02.2021 – Messalonskee 2, Winslow 0 |
3:30 PM 10.07.2021 – Nokomis at Winslow |
11 AM 10.09.2021 – Winslow at Belfast |
| 10.12.2021 – Winslow 9, Waterville 1 |
3 PM 10.14.2021 – Lawrence at Winslow |
| 10.15.2021 – Winslow 2, Leavitt 1 |
| 10.18.2021 – Oceanside at Winslow |
| 10.18.2021 – Winslow 5, Oceanside 0 |
| |
| 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 |
| |
| Soccer - Boys |
| 9.04.2021 – Winslow 4, Maine Central Institute 0 |
| 9.10.2021 – Winslow 4, Belfast 1 |
| 9.14.2021 – Winslow 6, Oceanside 0 |
| 9.21.2021 – Winslow 10, Belfast 0 |
6 PM 10.08.2021 – Winslow at Lawrence |
3:30 PM 10.15.2021 – Oceanside at Winslow |
| 10.19.2021 – Winslow 3, Waterville 0 |
| |
| Soccer - Girls |
| 9.04.2021 – Maine Central Institute 3, Winslow 0 |
| 9.07.2021 – Winslow 5, Cony 2 |
| 9.18.2021 – Winslow 1, Waterville 1 |
3:30 PM 10.08.2021 – Lawrence at Winslow |
3:30 PM 10.15.2021 – Oceanside at Winslow |
| 10.18.2021 – Waterville 1, Winslow 1 |
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