| All Schools |
| |
| Basketball - Boys |
| 12.07.2019 – Old Orchard Beach 95, Saint Dominic 53 |
| 12.10.2019 – Old Orchard Beach 77, Richmond 45 |
| 12.13.2019 – Waynflete 61, Old Orchard Beach 51 |
| 12.20.2019 – Lake Region 67, Old Orchard Beach 56 |
| 12.27.2019 – Poland Regional 74, Old Orchard Beach 64 |
| 1.04.2020 – Waynflete 67, Old Orchard Beach 48 |
| 1.07.2020 – Old Orchard Beach 71, Richmond 49 |
| 1.09.2020 – Cape Elizabeth 54, Old Orchard Beach 44 |
| 1.11.2020 – Old Orchard Beach 81, Sacopee Valley 56 |
| 1.14.2020 – Poland Regional 84, Old Orchard Beach 63 |
| 1.17.2020 – Old Orchard Beach 62, North Yarmouth Academy 55 |
| 1.21.2020 – Old Orchard Beach 77, Traip Academy 67 |
| 1.22.2020 – Old Orchard Beach 51, Buckfield 45 |
| 1.28.2020 – Old Orchard Beach 81, Saint Dominic 45 |
| 1.31.2020 – Old Orchard Beach 77, Sacopee Valley 56 |
| 2.04.2020 – North Yarmouth Academy 79, Old Orchard Beach 49 |
| 2.12.2020 – Monmouth Academy 62, Old Orchard Beach 53 |
| |
| Basketball - Girls |
| 12.07.2019 – Saint Dominic 43, Old Orchard Beach 33 |
| 12.10.2019 – Old Orchard Beach 48, Richmond 29 |
| 12.13.2019 – Old Orchard Beach 57, Waynflete 43 |
| 12.16.2019 – Wells 54, Old Orchard Beach 19 |
| 12.19.2019 – Old Orchard Beach 40, Lake Region 32 |
| 1.04.2020 – Old Orchard Beach 56, Waynflete 33 |
| 1.07.2020 – Old Orchard Beach 54, Richmond 25 |
| 1.09.2020 – Cape Elizabeth 54, Old Orchard Beach 38 |
| 1.11.2020 – Old Orchard Beach 44, Sacopee Valley 25 |
| 1.14.2020 – Old Orchard Beach 42, Poland Regional 27 |
| 1.17.2020 – North Yarmouth Academy 49, Old Orchard Beach 36 |
| 1.21.2020 – Old Orchard Beach 50, Traip Academy 38 |
| 1.22.2020 – Old Orchard Beach 69, Hebron Academy 13 |
| 1.28.2020 – Old Orchard Beach 52, Saint Dominic 49 |
| 1.31.2020 – Sacopee Valley 37, Old Orchard Beach 32 |
| 2.04.2020 – Old Orchard Beach 51, North Yarmouth Academy 49 |
| 2.11.2020 – Old Orchard Beach 72, Buckfield 22 |
| 2.18.2020 – Old Orchard Beach 45, Richmond 24 |
| 2.20.2020 – Winthrop 62, Old Orchard Beach 36 |
| |
| 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 |
| 10.19.2019 – Old Orchard Beach 50, Gray-New Gloucester 22 |
| 10.25.2019 – Old Orchard Beach 44, Boothbay Region 30 |
| 11.08.2019 – Old Orchard Beach 48, Boothbay Region 14 |
| 11.16.2019 – Mount Ararat 58, Old Orchard Beach 25 |
| |
| 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 |
| 10.14.2019 – Old Orchard Beach 4, Waynflete 2 |
| 10.16.2019 – Sacopee Valley 4, Old Orchard Beach 1 |
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