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| 21.07.2023 | 20:45 | Kerry FC | - | Ringmahon Rangers | 2:0 (0:0) | |
| 20:45 | Drogheda United | - | Sligo Rovers | 2:1 (0:1) | ||
| 20:45 | Kilbarrack United | - | Finn Harps | 0:1 (0:1) | ||
| 20:45 | Wexford FC | - | Avondale United | 3:0 (1:0) | ||
| 20:45 | UC Dublin | - | Cobh Ramblers | 3:2 (1:1) | ||
| 20:45 | Bohemian FC | - | Shelbourne FC | 1:0 (1:0) | ||
| 22.07.2023 | 15:00 | Treaty United | - | Cork City | 0:2 (0:0) | |
| 15:00 | Cockhill Celtic | - | Bray Wanderers | 1:3 (1:3) | ||
| 16:00 | Gorey Rangers | - | Rockmount AFC | 1:2 (0:1) | ||
| 18:00 | Galway United | - | Bangor Celtic | 4:1 (3:1) | ||
| 18:00 | St. Michaels FC | - | Waterford FC | 0:5 (0:3) | ||
| 23.07.2023 | 12:00 | Lucan United | - | St. Patrick's CYFC | 2:3 (1:2) | |
| 15:00 | Portlaoise AFC | - | Skerries Town | 0:3 (0:1) | ||
| 18:00 | Dundalk FC | - | Shamrock Rovers | 1:0 (1:0) | ||
| 18:00 | Derry City | - | Athlone Town | 3:0 (1:0) | ||
| 19:00 | Longford Town | - | St Patrick's Athletic | 1:2 (0:0) |
