| All Schools |
| |
| Basketball - Boys |
| 12.07.2018 – Winslow 56, Mount View 40 |
| 12.11.2018 – Winslow 63, Belfast 46 |
| 12.15.2018 – Orono 52, Winslow 41 |
| 12.18.2018 – Maranacook 63, Winslow 52 |
| 12.22.2018 – Winslow 51, Foxcroft Academy 46 |
| 12.27.2018 – Winslow 50, Waterville 48 |
| 1.02.2019 – Oceanside 60, Winslow 40 |
| 1.05.2019 – Winslow 55, Orono 47 |
| 1.10.2019 – Maine Central Institute 63, Winslow 52 |
| 1.12.2019 – Winslow 62, Foxcroft Academy 49 |
| 1.15.2019 – Oceanside 61, Winslow 55 |
| 1.17.2019 – Winslow 59, Mount View 38 |
| 1.21.2019 – Winslow 62, Belfast 58 |
| 1.25.2019 – Lawrence 66, Winslow 45 |
| 1.29.2019 – Skowhegan 56, Winslow 52 |
| 2.01.2019 – Winslow 78, Waterville 38 |
| 2.05.2019 – Maranacook 63, Winslow 44 |
| 2.07.2019 – Maine Central Institute 61, Winslow 52 |
| 2.12.2019 – Ellsworth 68, Winslow 43 |
| |
| Basketball - Girls |
| 12.07.2018 – Winslow 60, Mount View 28 |
| 12.11.2018 – Winslow 74, Belfast 31 |
| 12.15.2018 – Winslow 59, Orono 45 |
| 12.18.2018 – Winslow 65, Maranacook 30 |
| 12.22.2018 – Winslow 64, Foxcroft Academy 30 |
| 12.27.2018 – Waterville 42, Winslow 36 |
| 1.02.2019 – Oceanside 52, Winslow 48 |
| 1.05.2019 – Winslow 51, Orono 24 |
| 1.10.2019 – Winslow 53, Maine Central Institute 49 |
| 1.12.2019 – Foxcroft Academy 53, Winslow 41 |
| 1.15.2019 – Winslow 54, Oceanside 30 |
| 1.17.2019 – Winslow 51, Mount View 27 |
| 1.21.2019 – Winslow 66, Belfast 21 |
| 1.25.2019 – Lawrence 69, Winslow 49 |
| 1.29.2019 – Skowhegan 22, Winslow 14 |
| 2.01.2019 – Waterville 42, Winslow 41 |
| 2.05.2019 – Winslow 50, Maranacook 30 |
| 2.07.2019 – Winslow 58, Maine Central Institute 39 |
| 2.16.2019 – Winslow 36, Old Town 29 |
| |
| Field Hockey |
| 8.30.2018 – Winslow 5, Mount View 0 |
| 9.04.2018 – Belfast 5, Winslow 3 |
| 9.13.2018 – Winslow 2, Nokomis 0 |
| 9.15.2018 – Winslow 2, Lawrence 0 |
| 9.20.2018 – Winslow 3, Leavitt 1 |
| 9.22.2018 – Winslow 2, Lawrence 1 |
| 9.27.2018 – Winslow 8, Waterville 0 |
| 10.01.2018 – Winslow 8, Maranacook 1 |
| 10.04.2018 – Gardiner 3, Winslow 0 |
| 10.06.2018 – Winslow 4, Maine Central Institute 3 |
| 10.10.2018 – Winslow 10, Lincoln Academy 0 |
| 10.16.2018 – Winslow 3, Lawrence 0 |
| 10.19.2018 – Winslow 2, Foxcroft Academy 1 |
| 10.20.2018 – Winslow 2, Foxcroft Academy 1 |
| 10.24.2018 – Gardiner 3, Winslow 2 |
| |
| Football |
| 9.01.2018 – Winslow 28, Nokomis 20 |
| 9.07.2018 – Gardiner 35, Winslow 30 |
| 9.15.2018 – Winslow 54, Waterville 13 |
| 9.21.2018 – Winslow 26, Mount Desert Island 14 |
| 9.29.2018 – Lawrence 17, Winslow 14 |
| 10.06.2018 – Maine Central Institute 28, Winslow 7 |
| 10.13.2018 – Winslow 35, Medomak Valley 0 |
| 10.20.2018 – Winslow 78, Old Town 0 |
| 10.27.2018 – Winslow 46, Waterville 28 |
| 11.02.2018 – Hermon 20, Winslow 13 |
| |
| Soccer - Boys |
| 8.31.2018 – Gardiner 5, Winslow 3 |
| 9.04.2018 – Winslow 4, Lawrence 2 |
| 9.08.2018 – Winslow 3, Waterville 0 |
| 9.14.2018 – Brewer 2, Winslow 1 |
| 9.18.2018 – Bangor 5, Winslow 1 |
| 9.20.2018 – Winslow 4, Lawrence 3 |
| 9.22.2018 – Winslow 3, Erskine Academy 1 |
| 9.26.2018 – Winslow 3, Belfast 1 |
| 9.29.2018 – Winslow 4, Nokomis 2 |
| 10.05.2018 – Waterville 2, Winslow 0 |
| 10.09.2018 – Erskine Academy 1, Winslow 1 |
| 10.15.2018 – Winslow 5, Maine Central Institute 2 |
| 10.19.2018 – Old Town 2, Winslow 0 |
| |
| Soccer - Girls |
| 8.31.2018 – Winslow 3, Gardiner 0 |
| 9.04.2018 – Winslow 6, Lawrence 0 |
| 9.08.2018 – Winslow 4, Waterville 0 |
| 9.14.2018 – Winslow 2, Brewer 1 |
| 9.18.2018 – Bangor 3, Winslow 1 |
| 9.20.2018 – Winslow 12, Lawrence 0 |
| 9.22.2018 – Winslow 3, Erskine Academy 1 |
| 9.26.2018 – Winslow 6, Belfast 2 |
| 9.28.2018 – Winslow 5, Nokomis 1 |
| 10.05.2018 – Winslow 2, Waterville 1 |
| 10.08.2018 – Winslow 1, Erskine Academy 0 |
| 10.16.2018 – Winslow 3, Maranacook 0 |
| 10.20.2018 – Winslow 5, Foxcroft Academy 1 |
| 10.24.2018 – Winslow 2, Oceanside 1 |
| 10.29.2018 – Winslow 3, Hermon 0 |
| 10.31.2018 – Presque Isle 2, Winslow 0 |
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