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| All Schools |
| All Sports |
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| Field Hockey | | 8.31.2023 – Scarborough 3, Windham 2 |
| 9.05.2023 – Windham 6, South Portland/Westbrook 1 |
| 9.11.2023 – Kennebunk 1, Windham 0 |
| 9.13.2023 – Scarborough 3, Windham 1 |
| 9.19.2023 – Windham 3, Noble 2 |
| 9.23.2023 – Windham 2, Biddeford 1 |
| 9.25.2023 – Falmouth 3, Windham 2 |
| 9.27.2023 – Massabesic 3, Windham 1 |
| 9.29.2023 – Windham 4, Bonny Eagle 1 |
| 10.07.2023 – Cheverus 7, Windham 0 |
| 10.11.2023 – Thornton Academy 1, Windham 0 |
| 10.13.2023 – Gorham 8, Windham 1 |
| 10.14.2023 – Windham 7, Portland/Deering 1 |
| 10.17.2023 – Marshwood 4, Windham 2 |
| 10.20.2023 – Sanford 6, Windham 1 |
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