| 23. Round | 14/07/2023 | Finn Harps | - | Cobh Ramblers | 4:3 | ||||
| 24. Round | 29/07/2023 | Longford Town | - | Cobh Ramblers | 0:1 | ||||
| 26. Round | 07/08/2023 | Kerry FC | - | Cobh Ramblers | 2:2 | ||||
| 27. Round | 11/08/2023 | Cobh Ramblers | - | Bray Wanderers | 3:3 | ||||
| 28. Round | 25/08/2023 | Galway United | - | Cobh Ramblers | 4:1 | ||||
| 30. Round | 09/09/2023 | Cobh Ramblers | - | Athlone Town | 1:0 | ||||
| 32. Round | 22/09/2023 | Cobh Ramblers | - | Finn Harps | 5:1 | ||||
| 34. Round | 06/10/2023 | Cobh Ramblers | - | Longford Town | 2:0 | ||||
| 35. Round | 15/10/2023 | Wexford FC | - | Cobh Ramblers | 3:3 | ||||
| 36. Round | 20/10/2023 | Cobh Ramblers | - | Kerry FC | 1:1 |  |
Ireland