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| 27.08.2021 | 20:45 | Waterford FC | - | Kilnamanagh AFC | 4:1 (1:0) | |
| 20:45 | Dundalk FC | - | St. Mochta's | 5:1 (1:1) | ||
| 20:45 | Cork City | - | St Patrick's Athletic | 1:4 (0:0, 1:1, 1:1) pn. | ||
| 20:45 | UC Dublin | - | Longford Town | 2:1 (0:0) | ||
| 21:00 | Finn Harps | - | Derry City | 1:0 (0:0) | ||
| 28.08.2021 | 20:00 | Maynooth University Town | - | Cobh Ramblers | 3:2 (1:1) | |
| 29.08.2021 | 15:00 | Killester Donnycarney FC | - | Wexford FC | 0:2 (0:0) | |
| 17:00 | Bohemian FC | - | Shamrock Rovers | 2:1 (0:0) |
