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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.01.2023 – Westbrook 4, Noble 0 |
| 9.05.2023 – Windham 7, Westbrook 0 |
| 9.07.2023 – Deering 4, Westbrook 3 |
| 9.12.2023 – Westbrook 2, Thornton Academy 2 |
| 9.14.2023 – Westbrook 2, Biddeford 1 |
| 9.19.2023 – Westbrook 3, Marshwood 1 |
| 9.21.2023 – Portland 5, Westbrook 0 |
| 9.23.2023 – Westbrook 4, Cheverus 3 |
| 9.26.2023 – Bonny Eagle 1, Westbrook 0 |
| 9.28.2023 – Kennebunk 3, Westbrook 2 |
| 10.03.2023 – Westbrook 7, Massabesic 0 |
| 10.05.2023 – Westbrook 3, Sanford 1 |
| 10.10.2023 – Scarborough 3, Westbrook 0 |
| 10.17.2023 – Westbrook 3, South Portland 1 |
| 10.20.2023 – Falmouth 4, Westbrook 1 |
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