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| 28.08.2020 | 20:45 | Athlone Town | - | Wexford FC | 5:3 (0:2, 3:3) pró. | |
| 20:45 | Galway United | - | Shelbourne FC | 2:5 (0:1) | ||
| 29.08.2020 | 18:00 | Drogheda United | - | Derry City | 0:2 (0:0) | |
| 20:45 | Bray Wanderers | - | Finn Harps | 0:2 (0:2) | ||
| 30.08.2020 | 18:00 | Cobh Ramblers | - | Dundalk FC | 0:2 (0:1) | |
| 20:45 | UC Dublin | - | Sligo Rovers | 1:3 (1:1) | ||
| 31.08.2020 | 18:45 | Shamrock Rovers | - | Cork City | 2:1 (1:0) | |
| 20:45 | Bohemian FC | - | Cabinteely FC | 2:0 (2:0) |
