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| All Schools |
| All Sports |
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| Football | | 9.01.2023 – Westbrook 36, Biddeford 20 |
| 9.08.2023 – Fryeburg Academy 54, Westbrook 14 |
| 9.15.2023 – Kennebunk 35, Westbrook 0 |
| 9.23.2023 – Massabesic 34, Westbrook 33 |
| 9.29.2023 – Westbrook 40, Gorham 14 |
| 10.06.2023 – Marshwood 20, Westbrook 14 |
| 10.14.2023 – Cheverus 27, Westbrook 22 |
| 10.20.2023 – Westbrook 29, Deering 12 |
| 10.31.2023 – Westbrook 30, Deering 22 |
| 11.06.2023 – Kennebunk 23, Westbrook 22 |
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