| 1. Round | 26/03/2021 | Wexford FC | - | Cabinteely FC | 1:2 | ||||
| 6. Round | 30/04/2021 | Athlone Town | - | Cabinteely FC | 1:2 | ||||
| 7. Round | 07/05/2021 | Cabinteely FC | - | Cobh Ramblers | 1:0 |  |
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| 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 | ||||
| 16. Round | 17/07/2021 | Cobh Ramblers | - | Cabinteely FC | 1:0 | ||||
| 17. Round | 30/07/2021 | Cabinteely FC | - | Bray Wanderers | 0:3 |  |
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| 18. Round | 06/08/2021 | Treaty United | - | Cabinteely FC | 1:4 | ||||
| 20. Round | 20/08/2021 | Cabinteely FC | - | Cork City | 2:2 | ||||
| 21. Round | 03/09/2021 | Cabinteely FC | - | Galway United | 0:1 | ||||
| 22. Round | 10/09/2021 | UC Dublin | - | Cabinteely FC | 5:2 | |
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| 23. Round | 24/09/2021 | Cabinteely FC | - | Shelbourne FC | 0:2 | ||||
| 24. Round | 01/10/2021 | Athlone Town | - | Cabinteely FC | 2:1 | ||||
| 25. Round | 08/10/2021 | Cabinteely FC | - | Cobh Ramblers | 1:2 | ||||
| 26. Round | 15/10/2021 | Bray Wanderers | - | Cabinteely FC | 1:2 | |
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| 27. Round | 29/10/2021 | Cabinteely FC | - | Treaty United | 0:2 |
Ireland