| All Schools |
| |
| Field Hockey |
| 9.05.2019 – Winslow 4, Nokomis 0 |
| 9.10.2019 – Winslow 8, Waterville 1 |
| 9.12.2019 – Winslow 4, Oceanside 0 |
| 9.14.2019 – Winslow 9, Lincoln Academy 1 |
| 9.17.2019 – Winslow 8, Maranacook 0 |
| 9.19.2019 – Winslow 3, Leavitt 1 |
| 9.21.2019 – Winslow 5, Maine Central Institute 0 |
| 9.26.2019 – Winslow 9, Erskine Academy 1 |
| 9.28.2019 – Winslow 4, Mount View 0 |
| 9.30.2019 – Winslow 8, Morse 2 |
| 10.08.2019 – Foxcroft Academy 1, Winslow 0 |
| 10.10.2019 – Winslow 5, Lawrence 0 |
03:30 PM 10.16.2019 – Winslow at Belfast |
| |
| Football |
| 9.06.2019 – Wells 18, Winslow 6 |
| 9.14.2019 – Winslow 62, Nokomis 0 |
| 9.20.2019 – Winslow 76, Medomak Valley 6 |
| 9.28.2019 – Winslow 69, Foxcroft Academy 21 |
| 10.05.2019 – Winslow 55, Oceanside 0 |
| 10.11.2019 – Winslow 61, Maine Central Institute 37 |
01:00 PM 10.19.2019 – Hermon at Winslow |
01:00 PM 10.26.2019 – Winslow at Waterville |
| |
| Soccer - Boys |
| 9.06.2019 – Winslow 8, Morse 2 |
| 9.10.2019 – Winslow 3, Maranacook 2 |
| 9.12.2019 – Brewer 4, Winslow 2 |
| 9.19.2019 – Winslow 3, Lincoln Academy 2 |
| 9.21.2019 – Messalonskee 1, Winslow 1 |
| 9.25.2019 – Winslow 2, Oceanside 0 |
| 9.26.2019 – Maine Central Institute 4, Winslow 3 |
| 9.28.2019 – Winslow 3, Waterville 0 |
| 10.01.2019 – Winslow 3, Gardiner 1 |
| 10.03.2019 – Winslow 3, Lawrence 1 |
| 10.05.2019 – Winslow 2, Waterville 1 |
03:30 PM 10.15.2019 – Winslow at Nokomis |
03:30 PM 10.18.2019 – Mount View at Winslow |
03:30 PM 10.22.2019 – Winslow at Erskine Academy |
| |
| Soccer - Girls |
| 9.06.2019 – Winslow 3, Morse 1 |
| 9.10.2019 – Winslow 3, Maranacook 3 |
| 9.12.2019 – Winslow 3, Brewer 1 |
| 9.19.2019 – Lincoln Academy 4, Winslow 0 |
| 9.21.2019 – Winslow 1, Messalonskee 1 |
| 9.25.2019 – Winslow 10, Oceanside 0 |
| 9.26.2019 – Maine Central Institute 4, Winslow 0 |
| 9.28.2019 – Waterville 1, Winslow 0 |
| 10.03.2019 – Winslow 10, Lawrence 2 |
| 10.05.2019 – Waterville 5, Winslow 1 |
03:30 PM 10.15.2019 – Nokomis at Winslow |
03:30 PM 10.18.2019 – Winslow at Mount View |
03:30 PM 10.21.2019 – Erskine Academy at Winslow |
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