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| All Sports |
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| Football | | 8.31.2023 – Old Orchard Beach 64, Traip Academy 0 |
| 9.08.2023 – Old Orchard Beach 54, Dirigo 0 |
| 9.15.2023 – Old Orchard Beach 68, Boothbay Region 0 |
| 9.23.2023 – Old Orchard Beach 60, Telstar 0 |
| 9.30.2023 – Old Orchard Beach 82, Sacopee Valley 0 |
| 10.06.2023 – Old Orchard Beach 66, Maranacook 19 |
| 10.13.2023 – Old Orchard Beach 64, Mount View 13 |
| 10.20.2023 – Old Orchard Beach 66, Mount View 0 |
| 10.31.2023 – Old Orchard Beach 68, Sacopee Valley 0 |
| 11.04.2023 – Old Orchard Beach 56, Maranacook 8 |
| 11.11.2023 – Orono 46, Old Orchard Beach 18 |
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