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| All Schools |
| All Sports |
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| Field Hockey | | 9.06.2023 – Bonny Eagle 1, Portland/Deering 0 |
| 9.07.2023 – South Portland/Westbrook 2, Portland/Deering 0 |
| 9.11.2023 – Portland/Deering 3, Thornton Academy 2 |
| 9.14.2023 – Gorham 12, Portland/Deering 0 |
| 9.15.2023 – Marshwood 1, Portland/Deering 0 |
| 9.20.2023 – Massabesic 4, Portland/Deering 1 |
| 9.27.2023 – Portland/Deering 1, Kennebunk 0 |
| 9.28.2023 – Noble 4, Portland/Deering 2 |
| 10.03.2023 – Portland/Deering 1, Bonny Eagle 0 |
| 10.06.2023 – Falmouth 7, Portland/Deering 0 |
| 10.10.2023 – Sanford 5, Portland/Deering 0 |
| 10.11.2023 – South Portland/Westbrook 2, Portland/Deering 1 |
| 10.13.2023 – Portland/Deering 3, Kennebunk 0 |
| 10.14.2023 – Windham 7, Portland/Deering 1 |
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