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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.08.2021 – Falmouth 7, Massabesic 0 |
| 9.10.2021 – Bonny Eagle 3, Massabesic 0 |
| 9.13.2021 – Cheverus 7, Massabesic 0 |
| 9.18.2021 – Biddeford 6, Massabesic 2 |
| 9.22.2021 – Thornton Academy 4, Massabesic 0 |
| 9.29.2021 – Scarborough 9, Massabesic 0 |
| 10.02.2021 – South Portland 10, Massabesic 1 |
| 10.05.2021 – Portland 12, Massabesic 0 |
6:30 PM 10.08.2021 – Massabesic at Sanford |
| 10.09.2021 – Sanford 2, Massabesic 0 |
| 10.14.2021 – Westbrook 7, Massabesic 3 |
| 10.15.2021 – Noble 8, Massabesic 0 |
| 10.18.2021 – Kennebunk 5, Massabesic 0 |
| 10.21.2021 – Westbrook 5, Massabesic 0 |
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