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| 27/08/2021 | 19:45 | Waterford FC | - | Kilnamanagh AFC | 4:1 | |
| 19:45 | Dundalk FC | - | St. Mochta's | 5:1 | ||
| 19:45 | Cork City | - | St Patrick's Athletic | 1:4 pso | ||
| 19:45 | UC Dublin | - | Longford Town | 2:1 | ||
| 20:00 | Finn Harps | - | Derry City | 1:0 | ||
| 28/08/2021 | 19:00 | Maynooth University Town | - | Cobh Ramblers | 3:2 | |
| 29/08/2021 | 14:00 | Killester Donnycarney FC | - | Wexford FC | 0:2 | |
| 16:00 | Bohemian FC | - | Shamrock Rovers | 2:1 |
