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| 18.08.2023 | 20:45 | UC Dublin | - | Galway United | 0:2 | |
| 20:45 | Bohemian FC | - | Rockmount AFC | 6:0 (3:0) | ||
| 20:45 | Kerry FC | - | Drogheda United | 0:1 (0:1) | ||
| 20:45 | Bray Wanderers | - | Dundalk FC | 0:1 (0:0) | ||
| 21:00 | Finn Harps | - | Skerries Town | 5:0 (2:0) | ||
| 20.08.2023 | 14:30 | St. Patrick's CYFC | - | Wexford FC | 0:1 (0:1) | |
| 18:00 | Derry City | - | St Patrick's Athletic | 3:4 (0:0) i.E. | ||
| 21.08.2023 | 20:45 | Cork City | - | Waterford FC | 3:0 (2:0) |
