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| All Schools |
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| Football | | 9.03.2021 – Old Orchard Beach 26, Sacopee Valley 0 |
| 9.17.2021 – Telstar 26, Old Orchard Beach 6 |
| 10.01.2021 – Old Orchard Beach 53, Traip Academy 6 |
| 10.09.2021 – Dirigo 34, Old Orchard Beach 32 |
| 10.15.2021 – Mountain Valley 48, Old Orchard Beach 26 |
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| Soccer - Girls | | 9.02.2021 – North Yarmouth Academy 9, Old Orchard Beach 0 |
| 9.07.2021 – Old Orchard Beach 3, Sacopee Valley 2 |
| 9.10.2021 – Old Orchard Beach 3, Saint Dominic 1 |
| 9.14.2021 – Traip Academy 5, Old Orchard Beach 2 |
| 9.21.2021 – Old Orchard Beach 5, Poland Regional 2 |
| 9.25.2021 – Wells 9, Old Orchard Beach 1 |
| 9.28.2021 – Old Orchard Beach 2, Waynflete 0 |
| 10.02.2021 – Old Orchard Beach 9, Temple 0 |
| 10.04.2021 – North Yarmouth Academy 6, Old Orchard Beach 0 |
| 10.06.2021 – Old Orchard Beach 7, Temple 0 |
| 10.11.2021 – Sacopee Valley 6, Old Orchard Beach 0 |
| 10.13.2021 – Old Orchard Beach 4, Saint Dominic 1 |
| 10.15.2021 – Traip Academy 3, Old Orchard Beach 1 |
| 10.19.2021 – Old Orchard Beach 3, Waynflete 2 |
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