| 1. Round | 15/02/2019 | St Patrick's Athletic | - | Cork City | 1:0 | ||||
| 2. Round | 22/02/2019 | Cork City | - | Waterford FC | 0:2 | ||||
| 6. Round | 15/03/2019 | Cork City | - | Bohemian FC | 2:0 | ||||
| 8. Round | 29/03/2019 | Dundalk FC | - | Cork City | 1:0 | ||||
| 9. Round | 05/04/2019 | Cork City | - | Shamrock Rovers | 1:3 | ||||
| 10. Round | 12/04/2019 | Cork City | - | St Patrick's Athletic | 1:1 | ||||
| 14. Round | 29/04/2019 | Cork City | - | Finn Harps | 1:1 |  |
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| 15. Round | 03/05/2019 | Bohemian FC | - | Cork City | 0:1 | ||||
| 16. Round | 10/05/2019 | Cork City | - | UC Dublin | 2:0 |  |
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| 17. Round | 17/05/2019 | Cork City | - | Dundalk FC | 0:2 | |
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| 25. Round | 20/05/2019 | UC Dublin | - | Cork City | 0:1 | ||||
| 18. Round | 24/05/2019 | Shamrock Rovers | - | Cork City | 2:0 | ||||
| 19. Round | 31/05/2019 | St Patrick's Athletic | - | Cork City | 1:1 | ||||
| 21. Round | 14/06/2019 | Sligo Rovers | - | Cork City | 1:1 | ||||
| 22. Round | 28/06/2019 | Cork City | - | Derry City | 1:4 | ||||
| 27. Round | 28/07/2019 | Cork City | - | Shamrock Rovers | 1:1 | ||||
| 28. Round | 02/08/2019 | Cork City | - | St Patrick's Athletic | 0:1 | ||||
| 29. Round | 16/08/2019 | Waterford FC | - | Cork City | 1:2 |
Ireland