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| 06/09/2019 | 19:45 | Galway United | - | Shamrock Rovers | 1:2 (1:0) | |
| 07/09/2019 | 19:45 | Sligo Rovers | - | UC Dublin | 4:0 (2:0) | |
| 09/09/2019 | 19:45 | Waterford FC | - | Dundalk FC | 1:3 (0:3) | |
| 16/09/2019 | 19:45 | Crumlin United | - | Bohemian FC | 0:2 (0:1) |
|
|
|
|
| 06/09/2019 | 19:45 | Galway United | - | Shamrock Rovers | 1:2 (1:0) | |
| 07/09/2019 | 19:45 | Sligo Rovers | - | UC Dublin | 4:0 (2:0) | |
| 09/09/2019 | 19:45 | Waterford FC | - | Dundalk FC | 1:3 (0:3) | |
| 16/09/2019 | 19:45 | Crumlin United | - | Bohemian FC | 0:2 (0:1) |
