| 4. Round | 16/04/2021 | UC Dublin | - | Cabinteely FC | 4:1 | ||||
| 5. Round | 23/04/2021 | Cabinteely FC | - | Shelbourne FC | 1:3 |  |
|||
| 7. Round | 07/05/2021 | Cabinteely FC | - | Cobh Ramblers | 1:0 | ||||
| 8. Round | 14/05/2021 | Bray Wanderers | - | Cabinteely FC | 3:0 | ||||
| 9. Round | 21/05/2021 | Cabinteely FC | - | Treaty United | 2:1 | ||||
| 10. Round | 28/05/2021 | Cabinteely FC | - | Wexford FC | 0:2 | ||||
| 12. Round | 18/06/2021 | Galway United | - | Cabinteely FC | 1:0 | ||||
| 13. Round | 25/06/2021 | Cabinteely FC | - | UC Dublin | 1:2 | ||||
| 14. Round | 02/07/2021 | Shelbourne FC | - | Cabinteely FC | 1:0 | ||||
| 15. Round | 09/07/2021 | Cabinteely FC | - | Athlone Town | 0:1 | ||||
| 16. Round | 17/07/2021 | Cobh Ramblers | - | Cabinteely FC | 1:0 | ||||
| 20. Round | 20/08/2021 | Cabinteely FC | - | Cork City | 2:2 | ||||
| 22. Round | 10/09/2021 | UC Dublin | - | Cabinteely FC | 5:2 | ||||
| 23. Round | 24/09/2021 | Cabinteely FC | - | Shelbourne FC | 0:2 |
Ireland