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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.03.2022 – Windham 5, Westbrook 1 |
| 9.07.2022 – Windham 6, Bonny Eagle 1 |
| 9.09.2022 – Scarborough 2, Windham 0 |
| 9.12.2022 – Deering 3, Windham 0 |
| 9.14.2022 – Gorham 2, Windham 0 |
| 9.16.2022 – Portland 3, Windham 2 |
| 9.20.2022 – Windham 10, Massabesic 1 |
| 9.23.2022 – Windham 11, Noble 0 |
| 9.27.2022 – Windham 3, Falmouth 1 |
| 9.28.2022 – Windham 7, Sanford 1 |
| 10.03.2022 – Windham 2, South Portland 1 |
| 10.05.2022 – Windham 4, Cheverus 0 |
| 10.08.2022 – Windham 1, Thornton Academy 0 |
| 10.10.2022 – Windham 2, Biddeford 0 |
| 10.21.2022 – Windham 2, Thornton Academy 1 |
| 10.26.2022 – Windham 1, Marshwood 0 |
| 10.28.2022 – Windham 1, Deering 0 |
| 11.01.2022 – Scarborough 2, Windham 1 |
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