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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.03.2021 – Noble 1, Kennebunk 1 |
| 9.11.2021 – Deering 7, Kennebunk 1 |
| 9.14.2021 – Falmouth 1, Kennebunk 0 |
| 9.16.2021 – Kennebunk 2, Bonny Eagle 0 |
| 9.18.2021 – Cheverus 0, Kennebunk 0 |
| 9.22.2021 – Windham 3, Kennebunk 1 |
| 9.29.2021 – Thornton Academy 5, Kennebunk 0 |
| 10.01.2021 – Kennebunk 6, Westbrook 2 |
| 10.05.2021 – Scarborough 3, Kennebunk 0 |
| 10.08.2021 – South Portland 4, Kennebunk 0 |
| 10.13.2021 – Portland 4, Kennebunk 0 |
6 PM 10.16.2021 – Sanford at Kennebunk |
| 10.18.2021 – Kennebunk 5, Massabesic 0 |
| 10.22.2021 – Falmouth 3, Kennebunk 0 |
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