| 1. Round | 26/03/2021 | Cork City | - | Cobh Ramblers | 2:1 |  |
|||
| 2. Round | 03/04/2021 | Cobh Ramblers | - | UC Dublin | 0:4 | ||||
| 3. Round | 09/04/2021 | Treaty United | - | Cobh Ramblers | 1:1 | ||||
| 4. Round | 16/04/2021 | Wexford FC | - | Cobh Ramblers | 1:2 | |
|||
| 5. Round | 24/04/2021 | Cobh Ramblers | - | Bray Wanderers | 1:1 | ||||
| 11. Round | 11/06/2021 | UC Dublin | - | Cobh Ramblers | 1:2 | ||||
| 12. Round | 19/06/2021 | Cobh Ramblers | - | Treaty United | 0:2 | ||||
| 13. Round | 26/06/2021 | Cobh Ramblers | - | Wexford FC | 3:2 | |
|||
| 14. Round | 02/07/2021 | Bray Wanderers | - | Cobh Ramblers | 2:1 |  |
|||
| 15. Round | 09/07/2021 | Galway United | - | Cobh Ramblers | 2:0 | ||||
| 19. Round | 13/08/2021 | Cork City | - | Cobh Ramblers | 4:0 | ||||
| 20. Round | 21/08/2021 | Cobh Ramblers | - | UC Dublin | 0:2 | ||||
| 21. Round | 03/09/2021 | Treaty United | - | Cobh Ramblers | 3:0 | ||||
| 23. Round | 25/09/2021 | Cobh Ramblers | - | Bray Wanderers | 1:2 | ||||
| 24. Round | 01/10/2021 | Cobh Ramblers | - | Galway United | 0:1 |
Ireland