| All Schools |
| |
| Basketball - Boys |
| 12.06.2019 – Winslow 66, Mount View 52 |
| 12.10.2019 – Winslow 62, Belfast 52 |
| 12.14.2019 – Caribou 64, Winslow 41 |
| 12.18.2019 – Winslow 58, Oceanside 39 |
| 12.21.2019 – Winslow 48, Hermon 46 |
| 12.23.2019 – Winslow 68, Waterville 22 |
| 12.30.2019 – Maine Central Institute 71, Winslow 45 |
| 1.04.2020 – Hermon 39, Winslow 29 |
| 1.07.2020 – Maranacook 69, Winslow 60 |
| 1.09.2020 – Maine Central Institute 64, Winslow 53 |
| 1.11.2020 – Caribou 70, Winslow 50 |
| 1.14.2020 – Winslow 70, Lincoln Academy 44 |
| 1.24.2020 – Winslow 60, Belfast 49 |
| 1.28.2020 – Maranacook 65, Winslow 55 |
| 1.31.2020 – Winslow 58, Mount View 56 |
| 2.12.2020 – Winslow 62, Orono 52 |
| 2.14.2020 – Ellsworth 58, Winslow 51 |
| |
| Basketball - Girls |
| 12.06.2019 – Winslow 64, Mount View 26 |
| 12.10.2019 – Winslow 65, Belfast 30 |
| 12.14.2019 – Winslow 42, Caribou 33 |
| 12.21.2019 – Hermon 48, Winslow 38 |
| 12.23.2019 – Waterville 40, Winslow 33 |
| 12.30.2019 – Winslow 51, Maine Central Institute 26 |
| 1.04.2020 – Hermon 46, Winslow 39 |
| 1.07.2020 – Winslow 43, Maranacook 30 |
| 1.09.2020 – Winslow 84, Maine Central Institute 34 |
| 1.11.2020 – Winslow 56, Caribou 39 |
| 1.14.2020 – Lincoln Academy 49, Winslow 48 |
| 1.24.2020 – Winslow 64, Belfast 28 |
| 1.31.2020 – Winslow 57, Mount View 37 |
| 2.04.2020 – Winslow 51, Oceanside 46 |
| 2.11.2020 – Winslow 56, Caribou 35 |
| 2.14.2020 – Presque Isle 53, Winslow 46 |
| |
| 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 |
| 10.16.2019 – Belfast 3, Winslow 2 |
| 10.22.2019 – Winslow 9, John Bapst 0 |
| 10.25.2019 – Winslow 3, Lawrence 0 |
| 10.30.2019 – Winslow 5, Belfast 2 |
| 11.02.2019 – Winslow 7, York 2 |
| |
| 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 |
| 10.19.2019 – Winslow 37, Hermon 14 |
| 10.26.2019 – Winslow 57, Waterville 16 |
| 11.01.2019 – Winslow 42, Medomak Valley 6 |
| 11.09.2019 – Winslow 49, Hermon 7 |
| 11.16.2019 – Maine Central Institute 49, Winslow 21 |
| |
| 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 |
| 10.15.2019 – Winslow 4, Nokomis 2 |
| 10.18.2019 – Winslow 4, Mount View 1 |
| 10.22.2019 – Winslow 5, Erskine Academy 2 |
| 10.30.2019 – Foxcroft Academy 2, Winslow 1 |
| |
| 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 |
| 10.15.2019 – Winslow 3, Nokomis 0 |
| 10.18.2019 – Winslow 4, Mount View 1 |
| 10.21.2019 – Erskine Academy 0, Winslow 0 |
| 10.30.2019 – Mount Desert Island 6, Winslow 3 |
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