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| 28/08/2020 | 19:45 | Athlone Town | - | Wexford FC | 5:3 aet | |
| 19:45 | Galway United | - | Shelbourne FC | 2:5 | ||
| 29/08/2020 | 17:00 | Drogheda United | - | Derry City | 0:2 | |
| 19:45 | Bray Wanderers | - | Finn Harps | 0:2 | ||
| 30/08/2020 | 17:00 | Cobh Ramblers | - | Dundalk FC | 0:2 | |
| 19:45 | UC Dublin | - | Sligo Rovers | 1:3 | ||
| 31/08/2020 | 17:45 | Shamrock Rovers | - | Cork City | 2:1 | |
| 19:45 | Bohemian FC | - | Cabinteely FC | 2:0 |
