| All Schools |
| |
| 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 |
| |
| 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 |
| |
| Soccer - Girls |
| 9.06.2023 – Westbrook 3, Massabesic 3 |
| 9.09.2023 – Cheverus 7, Westbrook 1 |
| 9.13.2023 – Biddeford 5, Westbrook 4 |
| 9.20.2023 – Falmouth 7, Westbrook 1 |
| 9.22.2023 – Westbrook 2, Kennebunk 2 |
| 9.25.2023 – Noble 8, Westbrook 4 |
| 9.27.2023 – Marshwood 3, Westbrook 0 |
| 10.02.2023 – South Portland 4, Westbrook 0 |
| 10.04.2023 – Thornton Academy 8, Westbrook 0 |
| 10.09.2023 – Bonny Eagle 7, Westbrook 1 |
| 10.10.2023 – Portland 5, Westbrook 1 |
| 10.13.2023 – Deering 1, Westbrook 0 |
| 10.16.2023 – Westbrook 4, Massabesic 2 |
