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| All Schools |
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| Football | | 9.05.2019 – Old Orchard Beach 44, Telstar 28 |
| 9.13.2019 – Boothbay Region 46, Old Orchard Beach 30 |
| 9.21.2019 – Sacopee Valley 42, Old Orchard Beach 15 |
| 9.27.2019 – Old Orchard Beach 27, Traip Academy 8 |
| 10.05.2019 – Mount Ararat 46, Old Orchard Beach 8 |
| 10.12.2019 – Old Orchard Beach 50, Telstar 20 |
01:00 PM 10.19.2019 – Gray-New Gloucester at Old Orchard Beach |
07:00 PM 10.25.2019 – Boothbay Region at Old Orchard Beach |
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| Soccer - Girls | | 9.05.2019 – North Yarmouth Academy 5, Old Orchard Beach 0 |
| 9.09.2019 – Wells 5, Old Orchard Beach 2 |
| 9.13.2019 – Saint Dominic 1, Old Orchard Beach 0 |
| 9.18.2019 – Traip Academy 7, Old Orchard Beach 0 |
| 9.20.2019 – Old Orchard Beach 2, Waynflete 2 |
| 9.23.2019 – North Yarmouth Academy 8, Old Orchard Beach 3 |
| 9.26.2019 – Sacopee Valley 2, Old Orchard Beach 1 |
| 9.27.2019 – Lake Region 0, Old Orchard Beach 0 |
| 9.30.2019 – Gray-New Gloucester 4, Old Orchard Beach 1 |
| 10.04.2019 – Old Orchard Beach 2, Saint Dominic 1 |
| 10.11.2019 – Traip Academy 5, Old Orchard Beach 1 |
06:00 PM 10.14.2019 – Waynflete at Old Orchard Beach |
04:00 PM 10.16.2019 – Sacopee Valley at Old Orchard Beach |
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