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| 09.08.2019 | 20:00 | Cobh Wanderers | - | Limerick FC | 0:1 (0:0) | |
| 20:45 | St Patrick's Athletic | - | Bray Wanderers | 2:1 (0:1) | ||
| 20:45 | Bohemian FC | - | Shelbourne FC | 3:2 (0:0) | ||
| 20:45 | Cabinteely FC | - | Cork City | 4:5 (0:1, 1:1, 2:2) i.E. | ||
| 20:45 | Glebe North | - | Sligo Rovers | 0:8 (0:2) | ||
| 20:45 | Derry City | - | Wexford FC | 1:0 (0:0) | ||
| 20:45 | Drogheda United | - | Avondale United | 2:1 (1:0) | ||
| 21:00 | Shamrock Rovers | - | Finn Harps | 1:0 (1:0) | ||
| 10.08.2019 | 16:00 | St. Michaels FC | - | Glengad United | 7:8 (0:0, 0:0, 0:0) i.E. | |
| 19:00 | Crumlin United | - | Malahide United | 3:1 (3:1) | ||
| 20:00 | Cobh Ramblers | - | Dundalk FC | 0:1 (0:0) | ||
| 11.08.2019 | 12:00 | Lucan United | - | Killester Donnycarney FC | 2:1 (1:0) | |
| 15:00 | UC Dublin | - | Letterkenny Rovers | 5:2 (0:1) | ||
| 15:00 | Collinstown FC | - | Galway United | 1:2 (1:2) | ||
| 16:00 | Maynooth University Town | - | Waterford FC | 0:2 (0:1) | ||
| 13.08.2019 | 20:45 | Longford Town | - | Athlone Town | 3:1 (0:1) |
