| 1. Round | 26/03/2021 | Wexford FC | - | Cabinteely FC | 1:2 | ||||
| 2. Round | 02/04/2021 | Cabinteely FC | - | Cork City | 1:0 |  |
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| 4. Round | 16/04/2021 | UC Dublin | - | Cabinteely FC | 4:1 | |
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| 6. Round | 30/04/2021 | Athlone Town | - | Cabinteely FC | 1:2 | ||||
| 9. Round | 21/05/2021 | Cabinteely FC | - | Treaty United | 2:1 |  |
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| 10. Round | 28/05/2021 | Cabinteely FC | - | Wexford FC | 0:2 | ||||
| 11. Round | 11/06/2021 | Cork City | - | Cabinteely FC | 0:2 | |
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| 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 | |
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| 15. Round | 09/07/2021 | Cabinteely FC | - | Athlone Town | 0:1 | ||||
| 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 | ||||
| 20. Round | 20/08/2021 | Cabinteely FC | - | Cork City | 2:2 | ||||
| 21. Round | 03/09/2021 | Cabinteely FC | - | Galway United | 0:1 | |
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| 22. Round | 10/09/2021 | UC Dublin | - | Cabinteely FC | 5:2 | |
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| 24. Round | 01/10/2021 | Athlone Town | - | Cabinteely FC | 2:1 | |
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