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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.08.2021 – Windham 3, South Portland 0 |
| 9.11.2021 – Windham 2, Portland 0 |
| 9.14.2021 – Windham 3, Sanford 0 |
| 9.22.2021 – Windham 3, Kennebunk 1 |
| 9.25.2021 – Windham 2, Marshwood 0 |
| 9.29.2021 – Windham 2, Falmouth 1 |
| 10.02.2021 – Gorham 4, Windham 0 |
| 10.06.2021 – Windham 3, Cheverus 2 |
| 10.08.2021 – Windham 4, Deering 0 |
| 10.11.2021 – Windham 5, Noble 0 |
| 10.13.2021 – Windham 1, Biddeford 0 |
10 AM 10.16.2021 – Bonny Eagle at Windham |
| 10.18.2021 – Windham 3, Bonny Eagle 0 |
| 10.19.2021 – Windham 10, Westbrook 0 |
| 10.23.2021 – Windham 12, Westbrook 0 |
| 10.28.2021 – Windham 3, Portland 2 |
| 11.01.2021 – Marshwood 3, Windham 0 |
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