| All Schools |
| |
| 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 |
| |
| 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 |
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