| 17. Round | 30/07/2021 | Cabinteely FC | - | Bray Wanderers | 0:3 | ||||
| 18. Round | 06/08/2021 | Treaty United | - | Cabinteely FC | 1:4 |  |
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| 19. Round | 13/08/2021 | Wexford FC | - | Cabinteely FC | 2:1 | |
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| 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 | ||||
| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 |
England