| All Schools |
| |
| Field Hockey |
| 8.31.2023 – Cony 10, Winslow 0 |
| 9.02.2023 – Gardiner 8, Winslow 0 |
| 9.07.2023 – Belfast 5, Winslow 0 |
| 9.09.2023 – Dirigo 4, Winslow 0 |
| 9.19.2023 – Lawrence 7, Winslow 0 |
| 9.23.2023 – Morse 3, Winslow 2 |
| 9.25.2023 – Winslow 4, Lincoln Academy 0 |
| 9.27.2023 – Leavitt 5, Winslow 0 |
| 9.29.2023 – Winthrop/Monmouth/Maranacook 7, Winslow 0 |
| 10.05.2023 – Nokomis 5, Winslow 0 |
| 10.07.2023 – Maine Central Institute 3, Winslow 0 |
| 10.10.2023 – Winslow 2, Mount View 0 |
| 10.12.2023 – Oceanside 2, Winslow 0 |
| 10.16.2023 – Erskine Academy 4, Winslow 0 |
| |
| Football |
| 9.01.2023 – Winslow 25, Old Town 7 |
| 9.09.2023 – Winslow 16, Madison 14 |
| 9.18.2023 – Nokomis 36, Winslow 14 |
| 9.23.2023 – Belfast 41, Winslow 35 |
| 9.29.2023 – Lisbon 20, Winslow 19 |
| 10.07.2023 – Winslow 18, Brewer 16 |
| 10.14.2023 – Oak Hill 25, Winslow 13 |
| 10.21.2023 – Foxcroft Academy 35, Winslow 14 |
| 10.31.2023 – Winslow 55, Maine Central Institute 14 |
| 11.04.2023 – Foxcroft Academy 62, Winslow 7 |
| |
| Soccer - Boys |
| 9.01.2023 – Erskine Academy 3, Winslow 2 |
| 9.06.2023 – Morse 2, Winslow 0 |
| 9.08.2023 – Winslow 1, Gardiner 1 |
| 9.12.2023 – Winslow 11, Lawrence 0 |
| 9.21.2023 – Winslow 7, Mount View 0 |
| 9.23.2023 – Winslow 8, Maine Central Institute 0 |
| 9.26.2023 – Winslow 8, Nokomis 2 |
| 9.30.2023 – Winslow 6, Waterville 1 |
| 10.09.2023 – Winslow 3, Maine Central Institute 0 |
| 10.10.2023 – Winslow 3, Leavitt 0 |
| 10.13.2023 – Winslow 3, Waterville 1 |
| 10.17.2023 – Winslow 11, Lawrence 0 |
| 10.25.2023 – Winslow 4, Caribou 2 |
| 11.02.2023 – Ellsworth 3, Winslow 2 |
| |
| Soccer - Girls |
| 9.01.2023 – Erskine Academy 2, Winslow 1 |
| 9.06.2023 – Morse 3, Winslow 1 |
| 9.08.2023 – Gardiner 7, Winslow 2 |
| 9.12.2023 – Lawrence 2, Winslow 0 |
| 9.21.2023 – Winslow 4, Mount View 0 |
| 9.23.2023 – Maine Central Institute 3, Winslow 2 |
| 9.26.2023 – Winslow 2, Nokomis 0 |
| 9.28.2023 – Maine Central Institute 3, Winslow 2 |
| 9.30.2023 – Waterville 2, Winslow 1 |
| 10.03.2023 – Erskine Academy 0, Winslow 0 |
| 10.06.2023 – Winslow 3, Mount View 0 |
| 10.10.2023 – Leavitt 2, Winslow 1 |
| 10.12.2023 – Waterville 2, Winslow 0 |
| 10.17.2023 – Winslow 4, Lawrence 0 |
| 10.20.2023 – Gardiner 3, Winslow 1 |
