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| All Schools |
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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 |
3:30 pm 10.02.2023 – Boothbay Region at Oak Hill |
3:30 pm 10.04.2023 – Spruce Mountain at Boothbay Region |
3:30 pm 10.06.2023 – Dirigo at Boothbay Region |
3:30 pm 10.11.2023 – Boothbay Region at Winthrop/Monmouth/Maranacook |
3:30 pm 10.13.2023 – Hall-Dale at Boothbay Region |
3:30 pm 10.16.2023 – Lisbon at Boothbay Region |
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| Football | | 9.01.2023 – Maranacook 56, Boothbay Region 14 |
| 9.09.2023 – Boothbay Region 24, Traip Academy 12 |
| 9.15.2023 – Old Orchard Beach 68, Boothbay Region 0 |
| 9.23.2023 – Boothbay Region 50, Mount View 28 |
| 9.29.2023 – Boothbay Region 18, Telstar 8 |
7 pm 10.06.2023 – Sacopee Valley at Boothbay Region |
7 pm 10.13.2023 – Boothbay Region at Dirigo |
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