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| All Schools |
| All Sports |
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| Field Hockey | | 9.04.2021 – Scarborough 8, Portland/Deering 0 |
| 9.08.2021 – Bonny Eagle 4, Portland/Deering 0 |
| 9.11.2021 – Kennebunk 10, Portland/Deering 1 |
| 9.13.2021 – Westbrook 1, Portland/Deering 0 |
| 9.15.2021 – Windham 6, Portland/Deering 1 |
| 9.20.2021 – Thornton Academy 7, Portland/Deering 1 |
| 9.28.2021 – Portland/Deering 2, South Portland 0 |
| 10.04.2021 – Falmouth 5, Portland/Deering 0 |
| 10.06.2021 – Marshwood 4, Portland/Deering 1 |
| 10.08.2021 – Gorham 10, Portland/Deering 0 |
| 10.11.2021 – Cheverus 11, Portland/Deering 0 |
7 PM 10.19.2021 – Portland/Deering at Massabesic |
| 10.22.2021 – Scarborough 9, Portland/Deering 0 |
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