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| All Schools |
| All Sports |
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| Field Hockey | | 9.02.2022 – Massabesic 3, Portland/Deering 1 |
| 9.06.2022 – Noble 5, Portland/Deering 1 |
| 9.10.2022 – Sanford 8, Portland/Deering 0 |
| 9.14.2022 – South Portland/Westbrook 1, Portland/Deering 0 |
| 9.19.2022 – Biddeford 6, Portland/Deering 0 |
| 9.21.2022 – Cheverus 13, Portland/Deering 0 |
| 9.22.2022 – Gorham 9, Portland/Deering 0 |
| 9.26.2022 – Marshwood 3, Portland/Deering 0 |
| 10.03.2022 – Scarborough 11, Portland/Deering 0 |
| 10.05.2022 – Thornton Academy 5, Portland/Deering 0 |
| 10.08.2022 – Windham 2, Portland/Deering 0 |
| 10.13.2022 – Falmouth 3, Portland/Deering 0 |
| 10.15.2022 – Bonny Eagle 1, Portland/Deering 0 |
| 10.17.2022 – Kennebunk 4, Portland/Deering 1 |
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