| 3. Round | 09/04/2021 | Treaty United | - | Cobh Ramblers | 1:1 | ||||
| 13. Round | 26/06/2021 | Cobh Ramblers | - | Wexford FC | 3:2 |  |
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| 14. Round | 02/07/2021 | Bray Wanderers | - | Cobh Ramblers | 2:1 | ||||
| 15. Round | 09/07/2021 | Galway United | - | Cobh Ramblers | 2:0 | ||||
| 16. Round | 17/07/2021 | Cobh Ramblers | - | Cabinteely FC | 1:0 | ||||
| 20. Round | 21/08/2021 | Cobh Ramblers | - | UC Dublin | 0:2 | ||||
| 21. Round | 03/09/2021 | Treaty United | - | Cobh Ramblers | 3:0 | ||||
| 22. Round | 10/09/2021 | Wexford FC | - | Cobh Ramblers | 3:1 | ||||
| 23. Round | 25/09/2021 | Cobh Ramblers | - | Bray Wanderers | 1:2 | ||||
| 24. Round | 01/10/2021 | Cobh Ramblers | - | Galway United | 0:1 | ||||
| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 | ||||
| 26. Round | 15/10/2021 | Cobh Ramblers | - | Shelbourne FC | 2:0 | ||||
| 27. Round | 29/10/2021 | Athlone Town | - | Cobh Ramblers | 1:2 |
Ireland