| All Schools |
| |
| Field Hockey |
| 8.31.2023 – Scarborough 3, Windham 2 |
| 9.05.2023 – Windham 6, South Portland/Westbrook 1 |
| 9.11.2023 – Kennebunk 1, Windham 0 |
| 9.13.2023 – Scarborough 3, Windham 1 |
| 9.19.2023 – Windham 3, Noble 2 |
| 9.23.2023 – Windham 2, Biddeford 1 |
| 9.25.2023 – Falmouth 3, Windham 2 |
| 9.27.2023 – Massabesic 3, Windham 1 |
| 9.29.2023 – Windham 4, Bonny Eagle 1 |
| 10.07.2023 – Cheverus 7, Windham 0 |
| 10.11.2023 – Thornton Academy 1, Windham 0 |
| 10.13.2023 – Gorham 8, Windham 1 |
| 10.14.2023 – Windham 7, Portland/Deering 1 |
| 10.17.2023 – Marshwood 4, Windham 2 |
| 10.20.2023 – Sanford 6, Windham 1 |
| |
| Football |
| 9.01.2023 – Windham 35, Skowhegan 0 |
| 9.09.2023 – Windham 35, Bangor 6 |
| 9.15.2023 – Windham 48, Edward Little 0 |
| 9.22.2023 – Thornton Academy 37, Windham 6 |
| 9.29.2023 – Portland 35, Windham 7 |
| 10.06.2023 – Windham 21, Scarborough 3 |
| 10.13.2023 – Oxford Hills 35, Windham 14 |
| 10.20.2023 – Windham 33, Lewiston 0 |
| 10.31.2023 – Bonny Eagle 35, Windham 21 |
| 11.06.2023 – Oxford Hills 6, Windham 0 |
| |
| Soccer - Boys |
| 9.01.2023 – Windham 5, Kennebunk 3 |
| 9.05.2023 – Windham 7, Westbrook 0 |
| 9.07.2023 – Windham 4, Gorham 1 |
| 9.12.2023 – Windham 3, Scarborough 1 |
| 9.14.2023 – Windham 8, Noble 0 |
| 9.19.2023 – Windham 5, Biddeford 0 |
| 9.21.2023 – Windham 4, Cheverus 0 |
| 9.26.2023 – Falmouth 1, Windham 1 |
| 9.28.2023 – Windham 9, Massabesic 0 |
| 9.30.2023 – Windham 5, Marshwood 1 |
| 10.03.2023 – Windham 2, Deering 1 |
| 10.05.2023 – Windham 2, Thornton Academy 0 |
| 10.10.2023 – Windham 3, South Portland 1 |
| 10.13.2023 – Windham 4, Bonny Eagle 0 |
| 10.25.2023 – Windham 4, South Portland 0 |
| 11.02.2023 – Portland 1, Windham 0 |
| |
| Soccer - Girls |
| 8.31.2023 – Windham 2, Cheverus 0 |
| 9.09.2023 – Windham 6, Portland 0 |
| 9.14.2023 – Gorham 1, Windham 0 |
| 9.18.2023 – Falmouth 3, Windham 1 |
| 9.20.2023 – Windham 2, Bonny Eagle 0 |
| 9.25.2023 – Scarborough 3, Windham 0 |
| 9.27.2023 – Windham 2, Deering 0 |
| 9.30.2023 – Windham 2, South Portland 1 |
| 10.02.2023 – Windham 7, Noble 0 |
| 10.04.2023 – Windham 4, Kennebunk 1 |
| 10.06.2023 – Windham 4, Marshwood 2 |
| 10.09.2023 – Windham 3, Sanford 2 |
| 10.11.2023 – Windham 5, Thornton Academy 3 |
| 10.13.2023 – Windham 2, Cheverus 2 |
| 10.24.2023 – Windham 2, Falmouth 0 |
| 11.02.2023 – Gorham 2, Windham 1 |
