| 10. Round | 28/05/2021 | Cobh Ramblers | - | Cork City | 1:0 | ||||
| 11. Round | 11/06/2021 | UC Dublin | - | Cobh Ramblers | 1:2 | ||||
| 12. Round | 19/06/2021 | Cobh Ramblers | - | Treaty United | 0:2 | ||||
| 15. Round | 09/07/2021 | Galway United | - | Cobh Ramblers | 2:0 |  |
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| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 | |
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| 26. Round | 15/10/2021 | Cobh Ramblers | - | Shelbourne FC | 2:0 | ||||
| 27. Round | 29/10/2021 | Athlone Town | - | Cobh Ramblers | 1:2 |
Ireland