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| All Schools |
| All Sports |
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| Field Hockey | | 9.02.2021 – Windham 2, Noble 0 |
| 9.04.2021 – Windham 6, South Portland 0 |
| 9.08.2021 – Massabesic 2, Windham 1 |
| 9.10.2021 – Falmouth 3, Windham 2 |
| 9.14.2021 – Windham 3, Marshwood 2 |
| 9.15.2021 – Windham 6, Portland/Deering 1 |
| 9.22.2021 – Biddeford 8, Windham 2 |
| 9.28.2021 – Cheverus 5, Windham 0 |
| 9.30.2021 – Scarborough 4, Windham 0 |
| 10.02.2021 – Windham 2, Sanford 1 |
| 10.04.2021 – Bonny Eagle 1, Windham 1 |
| 10.06.2021 – Windham 3, Kennebunk 2 |
| 10.08.2021 – Windham 3, Westbrook 0 |
| 10.12.2021 – Windham 1, Gorham 0 |
| 10.21.2021 – Noble 3, Windham 2 |
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