| All Schools |
| |
| 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 |
| |
| Basketball - Boys |
| 1.22.2021 – Cony 73, Winslow 67 |
| 2.05.2021 – Winslow 57, Messalonskee 41 |
| 2.09.2021 – Lawrence 61, Winslow 57 |
| 2.11.2021 – Winslow 82, Waterville 20 |
| 2.12.2021 – Winslow 63, Cony 56 |
| 2.23.2021 – Winslow 65, Waterville 29 |
| 3.09.2021 – Skowhegan 74, Winslow 51 |
| |
| Basketball - Girls |
| 1.19.2021 – Erskine Academy 42, Winslow 41 |
| 1.28.2021 – Messalonskee 56, Winslow 39 |
| 2.11.2021 – Waterville 53, Winslow 41 |
| 2.23.2021 – Waterville 63, Winslow 44 |
| |
| Field Hockey |
| 9.25.2020 – Lawrence 3, Winslow 1 |
| 9.29.2020 – Skowhegan 2, Winslow 1 |
| 10.06.2020 – Winslow 9, Waterville 0 |
| 10.09.2020 – Winslow 3, Messalonskee 2 |
| 10.20.2020 – Skowhegan 5, Winslow 1 |
| |
| Soccer - Boys |
| 9.29.2020 – Waterville 4, Winslow 1 |
| 10.02.2020 – Winslow 1, Erskine Academy 0 |
| 10.07.2020 – Winslow 5, Lawrence 0 |
| 10.14.2020 – Winslow 1, Erskine Academy 0 |
| 10.24.2020 – Winslow 3, Waterville 1 |
| |
| Soccer - Girls |
| 9.28.2020 – Winslow 4, Gardiner 3 |
| 9.29.2020 – Waterville 4, Winslow 1 |
| 10.02.2020 – Erskine Academy 5, Winslow 2 |
| 10.07.2020 – Winslow 7, Lawrence 0 |
| 10.14.2020 – Erskine Academy 3, Winslow 1 |
| 10.23.2020 – Waterville 2, Winslow 1 |
| |
| Softball |
| 4.26.2021 – Waterville 9, Winslow 3 |
| 5.03.2021 – Hall-Dale 11, Winslow 2 |
| 5.21.2021 – Lawrence 9, Winslow 8 |
| 6.08.2021 – Winslow 9, Hermon 8 |
| 6.10.2021 – Winslow 6, Old Town 4 |
| 6.12.2021 – Winslow 6, Foxcroft Academy 3 |
| 6.16.2021 – Winslow 10, Nokomis 9 |
| 6.19.2021 – Cape Elizabeth 19, Winslow 4 |
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