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| All Schools |
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| Field Hockey | | 9.05.2023 – Windham 6, South Portland/Westbrook 1 |
| 9.07.2023 – South Portland/Westbrook 2, Portland/Deering 0 |
| 9.11.2023 – Falmouth 3, South Portland/Westbrook 0 |
| 9.14.2023 – Sanford 6, South Portland/Westbrook 3 |
| 9.20.2023 – Kennebunk 2, South Portland/Westbrook 0 |
| 9.25.2023 – Biddeford 9, South Portland/Westbrook 0 |
| 9.27.2023 – Thornton Academy 3, South Portland/Westbrook 1 |
| 9.29.2023 – Gorham 8, South Portland/Westbrook 0 |
| 10.03.2023 – Massabesic 5, South Portland/Westbrook 2 |
| 10.05.2023 – Marshwood 5, South Portland/Westbrook 0 |
| 10.09.2023 – Bonny Eagle 2, South Portland/Westbrook 1 |
| 10.11.2023 – South Portland/Westbrook 2, Portland/Deering 1 |
| 10.13.2023 – Cheverus 10, South Portland/Westbrook 0 |
| 10.17.2023 – Scarborough 4, South Portland/Westbrook 0 |
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