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| 23/07/2021 | 19:45 | Wexford FC | - | Cabinteely FC | 3:0 | |
| 19:45 | UC Dublin | - | Shelbourne FC | 2:0 | ||
| 19:45 | Athlone Town | - | Waterford FC | 2:4 (0:1, 3:3, 4:4) pso | ||
| 19:45 | St Patrick's Athletic | - | Bray Wanderers | 6:0 | ||
| 20:00 | St. Kevin's Boys | - | Kilnamanagh AFC | 1:4 | ||
| 20:00 | Shamrock Rovers | - | Galway United | 2:0 | ||
| 20:00 | Maynooth University Town | - | Malahide United | 4:0 | ||
| 24/07/2021 | 15:00 | Drogheda United | - | Derry City | 2:4 (1:0, 1:1, 1:1) pso | |
| 16:00 | Fairview Rangers | - | Finn Harps | 0:3 (0:0) aet | ||
| 19:30 | Longford Town | - | Bangor GG FC | 5:0 (1:0) | ||
| 25/07/2021 | 11:00 | Killester Donnycarney FC | - | Usher Celtic | 1:0 (0:0) | |
| 14:00 | Liffey Wanderers | - | Cobh Ramblers | 0:2 aet | ||
| 14:00 | Crumlin United | - | St. Mochta's | 1:2 | ||
| 14:00 | Treaty United | - | Dundalk FC | 0:1 aet | ||
| 15:00 | College Corinthians | - | Bohemian FC | 0:5 | ||
| 17:00 | Sligo Rovers | - | Cork City | 2:3 (1:1) |
