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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.07.2024 – Windham 3, Gorham 0 |
| 9.14.2024 – Windham 6, Bonny Eagle 0 |
| 9.16.2024 – Windham 1, Westbrook 0 |
| 9.18.2024 – Windham 2, Deering 0 |
| 9.21.2024 – Windham 7, Thornton Academy 0 |
| 9.25.2024 – Windham 3, Kennebunk 0 |
| 9.27.2024 – Windham 2, Marshwood 0 |
| 10.01.2024 – Scarborough 1, Windham 0 |
| 10.04.2024 – Windham 2, Biddeford 1 |
| 10.09.2024 – Falmouth 2, Windham 2 |
| 10.11.2024 – Windham 2, Portland 1 |
| 10.15.2024 – Windham 2, Cheverus 0 |
| 10.17.2024 – Windham 3, South Portland 0 |
| 10.21.2024 – Gorham 0, Windham 0 |
| 10.30.2024 – Windham 2, South Portland 1 |
TBA 11.01.2024 – Portland at Windham |
| 11.02.2024 – Portland 2, Windham 1 |
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