| 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 | ||||
| 6. Round | 01/05/2021 | Cobh Ramblers | - | Galway United | 0:4 | ||||
| 7. Round | 07/05/2021 | Cabinteely FC | - | Cobh Ramblers | 1:0 | ||||
| 8. Round | 15/05/2021 | Cobh Ramblers | - | Shelbourne FC | 1:2 | ||||
| 10. Round | 28/05/2021 | Cobh Ramblers | - | Cork City | 1:0 | ||||
| 14. Round | 02/07/2021 | Bray Wanderers | - | Cobh Ramblers | 2:1 | ||||
| 19. Round | 13/08/2021 | Cork City | - | Cobh Ramblers | 4:0 |
Ireland