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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.01.2023 – Windham 5, Kennebunk 3 |
| 9.07.2023 – Kennebunk 1, Marshwood 1 |
| 9.09.2023 – Kennebunk 3, Sanford 1 |
| 9.12.2023 – Kennebunk 8, Noble 2 |
| 9.14.2023 – Kennebunk 1, Scarborough 0 |
| 9.19.2023 – Kennebunk 4, Massabesic 0 |
| 9.21.2023 – Gorham 4, Kennebunk 1 |
| 9.26.2023 – Deering 4, Kennebunk 2 |
| 9.28.2023 – Kennebunk 3, Westbrook 2 |
| 9.30.2023 – Kennebunk 1, Portland 0 |
| 10.03.2023 – South Portland 3, Kennebunk 1 |
| 10.05.2023 – Kennebunk 3, Falmouth 1 |
| 10.10.2023 – Thornton Academy 1, Kennebunk 1 |
| 10.12.2023 – Kennebunk 3, Biddeford 1 |
| 10.21.2023 – Kennebunk 5, Biddeford 0 |
| 10.25.2023 – Deering 2, Kennebunk 1 |
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