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| All Sports |
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| Field Hockey | | 8.31.2023 – Oak Hill 3, Boothbay Region 2 |
| 9.11.2023 – Winthrop/Monmouth/Maranacook 8, Boothbay Region 1 |
| 9.13.2023 – Hall-Dale 4, Boothbay Region 0 |
| 9.15.2023 – Mountain Valley 3, Boothbay Region 1 |
| 9.21.2023 – Spruce Mountain 11, Boothbay Region 1 |
| 9.22.2023 – Boothbay Region 1, Telstar 0 |
| 9.25.2023 – Dirigo 6, Boothbay Region 0 |
| 9.27.2023 – Boothbay Region 2, Lisbon 1 |
| 10.02.2023 – Oak Hill 2, Boothbay Region 1 |
| 10.04.2023 – Spruce Mountain 3, Boothbay Region 1 |
| 10.06.2023 – Dirigo 4, Boothbay Region 3 |
| 10.11.2023 – Winthrop/Monmouth/Maranacook 10, Boothbay Region 1 |
| 10.13.2023 – Hall-Dale 3, Boothbay Region 0 |
| 10.16.2023 – Boothbay Region 4, Lisbon 2 |
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