| All Schools |
| |
| 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 |
| 10.06.2023 – Old Orchard Beach 66, Maranacook 19 |
| 10.13.2023 – Old Orchard Beach 64, Mount View 13 |
| 10.20.2023 – Old Orchard Beach 66, Mount View 0 |
| 10.31.2023 – Old Orchard Beach 68, Sacopee Valley 0 |
| 11.04.2023 – Old Orchard Beach 56, Maranacook 8 |
| 11.11.2023 – Orono 46, Old Orchard Beach 18 |
TBA 11.11.2023 – Orono at Old Orchard Beach |
| |
| 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 |
| 10.04.2023 – Old Orchard Beach 4, Buckfield 1 |
| 10.09.2023 – Traip Academy 2, Old Orchard Beach 0 |
| 10.10.2023 – Old Orchard Beach 5, Buckfield 2 |
| 10.16.2023 – Sacopee Valley 1, Old Orchard Beach 0 |
| 10.24.2023 – Old Orchard Beach 1, Temple 0 |
| 10.31.2023 – Saint Dominic 3, Old Orchard Beach 1 |
