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| All Schools |
| All Sports |
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| Soccer - Girls | | 9.07.2021 – Windham 3, South Portland 0 |
| 9.09.2021 – Windham 5, Portland 1 |
| 9.14.2021 – Windham 6, Sanford 1 |
| 9.16.2021 – Windham 8, Massabesic 0 |
| 9.18.2021 – Windham 6, Noble 0 |
| 9.21.2021 – Windham 5, Kennebunk 0 |
| 9.23.2021 – Windham 4, Marshwood 0 |
| 9.28.2021 – Windham 3, Falmouth 0 |
| 9.30.2021 – Windham 3, Gorham 1 |
| 10.05.2021 – Windham 2, Cheverus 1 |
| 10.07.2021 – Windham 5, Deering 0 |
| 10.12.2021 – Windham 8, Biddeford 1 |
| 10.14.2021 – Windham 4, Bonny Eagle 0 |
| 10.19.2021 – Windham 10, Westbrook 0 |
| 10.23.2021 – Windham 9, Massabesic 0 |
| 10.28.2021 – Windham 5, Noble 1 |
| 10.30.2021 – Windham 8, Thornton Academy 2 |
| 11.03.2021 – Windham 3, Gorham 0 |
| 11.06.2021 – Windham 3, Brunswick 1 |
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