| 24. Round | 05/07/2019 | Shamrock Rovers | - | Sligo Rovers | 0:0 | ||||
| 26. Round | 21/07/2019 | Shamrock Rovers | - | UC Dublin | 7:0 | ||||
| 27. Round | 28/07/2019 | Cork City | - | Shamrock Rovers | 1:1 | ||||
| 29. Round | 16/08/2019 | Derry City | - | Shamrock Rovers | 0:2 |  |
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| 19. Round | 19/08/2019 | Waterford FC | - | Shamrock Rovers | 1:5 | ||||
| 30. Round | 30/08/2019 | Shamrock Rovers | - | Bohemian FC | 1:0 | ||||
| 32. Round | 20/09/2019 | Shamrock Rovers | - | St Patrick's Athletic | 0:0 | ||||
| 31. Round | 23/09/2019 | Dundalk FC | - | Shamrock Rovers | 3:2 | ||||
| 33. Round | 05/10/2019 | Sligo Rovers | - | Shamrock Rovers | 0:0 | ||||
| 35. Round | 18/10/2019 | UC Dublin | - | Shamrock Rovers | 0:3 | ||||
| 36. Round | 25/10/2019 | Shamrock Rovers | - | Cork City | 3:0 |
Ireland