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| All Schools |
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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 |
7 pm 10.06.2023 – Old Orchard Beach at Maranacook |
1:30 pm 10.14.2023 – Mount View at Old Orchard Beach |
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| Soccer - Girls | | 8.31.2023 – Old Orchard Beach 3, Richmond 2 |
| 9.08.2023 – North Yarmouth Academy 5, Old Orchard Beach 0 |
| 9.14.2023 – Saint Dominic 3, Old Orchard Beach 0 |
| 9.18.2023 – Waynflete 8, Old Orchard Beach 0 |
| 9.19.2023 – Old Orchard Beach 6, Temple 0 |
| 9.21.2023 – Old Orchard Beach 3, Sacopee Valley 1 |
| 9.23.2023 – Richmond 3, Old Orchard Beach 2 |
| 9.25.2023 – Wells 2, Old Orchard Beach 0 |
| 9.27.2023 – Saint Dominic 3, Old Orchard Beach 1 |
| 9.30.2023 – Fryeburg Academy 3, Old Orchard Beach 0 |
4 pm 10.04.2023 – Old Orchard Beach at Buckfield |
7:45 pm 10.07.2023 – Old Orchard Beach at Traip Academy |
4 pm 10.10.2023 – Buckfield at Old Orchard Beach |
6 pm 10.16.2023 – Sacopee Valley at Old Orchard Beach |
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