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| All Schools |
| All Sports |
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| Soccer - Girls | | 8.31.2023 – Windham 2, Cheverus 0 |
| 9.09.2023 – Windham 6, Portland 0 |
| 9.14.2023 – Gorham 1, Windham 0 |
| 9.18.2023 – Falmouth 3, Windham 1 |
| 9.20.2023 – Windham 2, Bonny Eagle 0 |
| 9.25.2023 – Scarborough 3, Windham 0 |
| 9.27.2023 – Windham 2, Deering 0 |
| 9.30.2023 – Windham 2, South Portland 1 |
| 10.02.2023 – Windham 7, Noble 0 |
| 10.04.2023 – Windham 4, Kennebunk 1 |
| 10.06.2023 – Windham 4, Marshwood 2 |
| 10.09.2023 – Windham 3, Sanford 2 |
| 10.11.2023 – Windham 5, Thornton Academy 3 |
| 10.13.2023 – Windham 2, Cheverus 2 |
| 10.24.2023 – Windham 2, Falmouth 0 |
| 11.02.2023 – Gorham 2, Windham 1 |
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