| 24. Round | 05/07/2019 | Shamrock Rovers | - | Sligo Rovers | 0:0 | ||||
| 26. Round | 21/07/2019 | Shamrock Rovers | - | UC Dublin | 7:0 |  |
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| 27. Round | 28/07/2019 | Cork City | - | Shamrock Rovers | 1:1 |  |
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| 19. Round | 19/08/2019 | Waterford FC | - | Shamrock Rovers | 1:5 | ||||
| 28. Round | 27/08/2019 | Shamrock Rovers | - | Waterford FC | 2:1 | |
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| 33. Round | 05/10/2019 | Sligo Rovers | - | Shamrock Rovers | 0:0 | ||||
| 34. Round | 11/10/2019 | Shamrock Rovers | - | Finn Harps | 1:0 | ||||
| 35. Round | 18/10/2019 | UC Dublin | - | Shamrock Rovers | 0:3 | |
Ireland