| 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 |  |
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| 8. Round | 15/05/2021 | Cobh Ramblers | - | Shelbourne FC | 1:2 | ||||
| 9. Round | 21/05/2021 | Athlone Town | - | 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 | |
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| 17. Round | 30/07/2021 | Shelbourne FC | - | Cobh Ramblers | 2:2 | ||||
| 19. Round | 13/08/2021 | Cork City | - | Cobh Ramblers | 4:0 | |
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| 20. Round | 21/08/2021 | Cobh Ramblers | - | UC Dublin | 0:2 | |
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| 21. Round | 03/09/2021 | Treaty United | - | Cobh Ramblers | 3:0 | ||||
| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 | ||||
| 27. Round | 29/10/2021 | Athlone Town | - | Cobh Ramblers | 1:2 |
Ireland