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| 01/04/2019 | 19:00 | Waterford FC | - | Galway United | 2:1 (1:0) | |
| 19:45 | Bohemian FC | - | Cabinteely FC | 2:1 (0:1) | ||
| 19:45 | Bray Wanderers | - | Shamrock Rovers | 4:2 (0:0, 0:0, 0:0) pso | ||
| 19:45 | Cork City | - | Cobh Ramblers | 4:1 (1:0) | ||
| 19:45 | St Patrick's Athletic | - | Dundalk FC | 1:2 (1:2) | ||
| 20:00 | Finn Harps | - | Sligo Rovers | 2:1 (0:0, 1:1) aet | ||
| 02/04/2019 | 19:45 | Derry City | - | Longford Town | 3:0 (2:0) | |
| 19:45 | Shelbourne FC | - | UC Dublin | 1:2 (1:1) |
