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| All Schools |
| All Sports |
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| Baseball | | 4.20.2021 – Winslow 3, Maine Central Institute 2 |
| 4.23.2021 – Lawrence 15, Winslow 4 |
| 4.26.2021 – Winslow 13, Waterville 3 |
| 5.03.2021 – Winslow 11, Hall-Dale 1 |
| 5.10.2021 – Skowhegan 11, Winslow 6 |
| 5.12.2021 – Hall-Dale 8, Winslow 7 |
| 5.19.2021 – Winslow 9, Erskine Academy 8 |
| 5.21.2021 – Lawrence 3, Winslow 0 |
| 5.24.2021 – Gardiner 6, Winslow 0 |
| 6.08.2021 – Hermon 3, Winslow 2 |
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