| All Schools |
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| Baseball |
| 4.20.2021 – Sacopee Valley 10, Old Orchard Beach 1 |
| 4.24.2021 – NYA/Waynflete 10, Old Orchard Beach 0 |
| 4.24.2021 – NYA/Waynflete 10, Old Orchard Beach 0 |
| 5.03.2021 – Old Orchard Beach 7, Sacopee Valley 1 |
| 5.06.2021 – Old Orchard Beach 12, Traip Academy 6 |
| 5.07.2021 – Gray-New Gloucester 2, Old Orchard Beach 1 |
| 5.13.2021 – York 6, Old Orchard Beach 2 |
| 5.17.2021 – Wells 4, Old Orchard Beach 0 |
| 5.20.2021 – Cape Elizabeth 5, Old Orchard Beach 2 |
| 5.26.2021 – Old Orchard Beach 4, Lake Region 3 |
| 5.29.2021 – Old Orchard Beach 4, Saint Dominic 0 |
| 6.08.2021 – Dirigo 9, Old Orchard Beach 3 |
| |
| Basketball - Boys |
| 2.19.2021 – Old Orchard Beach 48, Traip Academy 33 |
| 3.13.2021 – Waynflete 57, Old Orchard Beach 33 |
| |
| Basketball - Girls |
| 2.19.2021 – Old Orchard Beach 50, Traip Academy 36 |
| 3.08.2021 – Old Orchard Beach 57, Bonny Eagle 56 |
| |
| Softball |
| 4.20.2021 – Sacopee Valley 9, Old Orchard Beach 5 |
| 4.20.2021 – Sacopee Valley 14, Old Orchard Beach 2 |
| 4.24.2021 – North Yarmouth Academy 12, Old Orchard Beach 0 |
| 4.26.2021 – North Yarmouth Academy 15, Old Orchard Beach 10 |
| 5.06.2021 – Traip Academy 11, Old Orchard Beach 9 |
| 5.07.2021 – Gray-New Gloucester 14, Old Orchard Beach 0 |
| 5.17.2021 – Wells 11, Old Orchard Beach 3 |
| 6.01.2021 – Old Orchard Beach 4, Saint Dominic 2 |
| 6.01.2021 – Saint Dominic 18, Old Orchard Beach 9 |
| 6.08.2021 – Monmouth Academy 12, Old Orchard Beach 4 |
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