| All Schools |
| |
| Baseball |
| 4.23.2021 – Biddeford 8, Windham 6 |
| 4.27.2021 – Thornton Academy 11, Windham 1 |
| 5.01.2021 – South Portland 9, Windham 6 |
| 5.04.2021 – Bonny Eagle 7, Windham 2 |
| 5.08.2021 – Gorham 6, Windham 0 |
| 5.15.2021 – Cheverus 10, Windham 0 |
| 5.15.2021 – Cheverus 3, Windham 0 |
| 5.18.2021 – Falmouth 7, Windham 0 |
| 5.25.2021 – Scarborough 5, Windham 4 |
| 5.29.2021 – Portland 3, Windham 2 |
| 6.01.2021 – Falmouth 13, Windham 4 |
| 6.05.2021 – Windham 3, Westbrook 0 |
| |
| Basketball - Boys |
| 2.09.2021 – Gorham 40, Windham 31 |
| 2.17.2021 – Windham 59, Lewiston 48 |
| 2.27.2021 – Gorham 61, Windham 53 |
| 3.03.2021 – Windham 63, Bonny Eagle 55 |
| 3.05.2021 – Windham 49, Bonny Eagle 47 |
| |
| Basketball - Girls |
| 2.09.2021 – Gorham 61, Windham 46 |
| 2.17.2021 – Windham 54, Lewiston 45 |
| 3.12.2021 – Windham 58, Gray-New Gloucester 19 |
| 3.13.2021 – Windham 53, Gorham 48 |
| |
| Field Hockey |
| 9.25.2020 – Windham 3, Westbrook 0 |
| 9.29.2020 – Windham 5, Gray-New Gloucester 0 |
| 10.02.2020 – Gorham 2, Windham 1 |
| 10.03.2020 – Gorham 2, Windham 1 |
| 10.09.2020 – Windham 9, Westbrook 0 |
| 10.14.2020 – Windham 4, Bonny Eagle 0 |
| 10.21.2020 – Windham 3, Bonny Eagle 2 |
| 10.23.2020 – Windham 2, Gorham 1 |
| 10.27.2020 – Windham 9, Sacopee Valley 1 |
| 11.04.2020 – Gorham 6, Windham 1 |
| |
| Ice Hockey |
| 2.25.2021 – Windham 3, Portland/Deering 2 |
| |
| Soccer - Boys |
| 9.26.2020 – Windham 1, Westbrook 0 |
| 10.03.2020 – Gorham 1, Windham 0 |
| 10.14.2020 – Windham 2, Bonny Eagle 1 |
| 10.20.2020 – Windham 4, Edward Little 2 |
| 10.22.2020 – Windham 4, Gray-New Gloucester 1 |
| 10.28.2020 – Windham 3, Bonny Eagle 1 |
| 11.06.2020 – Scarborough 1, Windham 0 |
| 11.10.2020 – Falmouth 6, Windham 0 |
| |
| Soccer - Girls |
| 9.26.2020 – Windham 11, Westbrook 0 |
| 10.03.2020 – Windham 3, Gorham 2 |
| 10.19.2020 – Windham 4, Gray-New Gloucester 0 |
| 10.20.2020 – Windham 7, Edward Little 0 |
| 10.26.2020 – Windham 3, Bonny Eagle 1 |
| 11.05.2020 – Scarborough 3, Windham 1 |
| |
| Softball |
| 4.23.2021 – Biddeford 16, Windham 4 |
| 5.06.2021 – Windham 13, Bonny Eagle 1 |
| 5.10.2021 – Windham 7, Gorham 2 |
| 5.11.2021 – Windham 6, Westbrook 0 |
| 5.14.2021 – Windham 4, Cheverus 0 |
| 5.19.2021 – Windham 14, Falmouth 0 |
| 5.26.2021 – Windham 8, Scarborough 2 |
| 5.28.2021 – Windham 10, Portland 2 |
| 5.28.2021 – Windham 4, Portland 1 |
| 6.08.2021 – Windham 9, Westbrook 2 |
| 6.10.2021 – Windham 17, Falmouth 0 |
| 6.12.2021 – Biddeford 3, Windham 2 |
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