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| All Schools |
| All Sports |
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| Field Hockey | | 9.04.2021 – Falmouth 4, Kennebunk 1 |
| 9.08.2021 – Kennebunk 3, Marshwood 1 |
| 9.11.2021 – Kennebunk 10, Portland/Deering 1 |
| 9.17.2021 – Biddeford 7, Kennebunk 3 |
| 9.22.2021 – Cheverus 3, Kennebunk 0 |
| 9.24.2021 – Scarborough 1, Kennebunk 0 |
| 9.28.2021 – Kennebunk 3, Bonny Eagle 0 |
| 10.04.2021 – Kennebunk 3, Westbrook 0 |
| 10.06.2021 – Windham 3, Kennebunk 2 |
| 10.08.2021 – Kennebunk 4, Thornton Academy 0 |
| 10.12.2021 – Massabesic 2, Kennebunk 1 |
| 10.14.2021 – Kennebunk 4, Noble 1 |
4 PM 10.15.2021 – Sanford at Kennebunk |
| 10.22.2021 – Kennebunk 1, Thornton Academy 0 |
| 10.27.2021 – Cheverus 5, Kennebunk 1 |
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