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| All Schools |
| All Sports |
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| Field Hockey | | 9.13.2021 – Westbrook 1, Portland/Deering 0 |
| 9.20.2021 – Biddeford 6, Westbrook 1 |
| 9.28.2021 – Scarborough 8, Westbrook 0 |
| 10.02.2021 – Marshwood 2, Westbrook 1 |
| 10.04.2021 – Kennebunk 3, Westbrook 0 |
| 10.07.2021 – Bonny Eagle 2, Westbrook 0 |
| 10.08.2021 – Windham 3, Westbrook 0 |
| 10.12.2021 – Westbrook 4, South Portland 0 |
| 10.13.2021 – Cheverus 11, Westbrook 1 |
| 10.15.2021 – Thornton Academy 5, Westbrook 1 |
| 10.18.2021 – Gorham 5, Westbrook 1 |
| 10.22.2021 – Massabesic 9, Westbrook 2 |
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