| 23. Round | 01/07/2019 | Sligo Rovers | - | UC Dublin | 5:1 | ||||
| 24. Round | 05/07/2019 | UC Dublin | - | Finn Harps | 1:0 |  |
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| 19. Round | 12/07/2019 | Derry City | - | UC Dublin | 0:0 | ||||
| 20. Round | 15/07/2019 | UC Dublin | - | Bohemian FC | 3:0 dec. | ||||
| 26. Round | 21/07/2019 | Shamrock Rovers | - | UC Dublin | 7:0 | ||||
| 27. Round | 26/07/2019 | UC Dublin | - | Waterford FC | 1:2 | ||||
| 28. Round | 02/08/2019 | UC Dublin | - | Derry City | 1:3 | ||||
| 29. Round | 16/08/2019 | Bohemian FC | - | UC Dublin | 10:1 | ||||
| 30. Round | 30/08/2019 | UC Dublin | - | Dundalk FC | 0:5 | ||||
| 31. Round | 13/09/2019 | St Patrick's Athletic | - | UC Dublin | 0:0 | |
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| 32. Round | 20/09/2019 | UC Dublin | - | Sligo Rovers | 0:2 | |
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| 33. Round | 04/10/2019 | Finn Harps | - | UC Dublin | 0:0 | ||||
| 34. Round | 11/10/2019 | Cork City | - | UC Dublin | 3:2 | |
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| 36. Round | 25/10/2019 | Waterford FC | - | UC Dublin | 4:2 | |
England