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| 04/05/2009 | 15:00 | FC Carlow | - | Waterford United | 1:2 aet | |
| 15:00 | Galway United (old) | - | Derry City | 1:0 | ||
| 15:00 | St Patrick's Athletic | - | Shamrock Rovers | 0:1 | ||
| 17:00 | Cork City | - | Wexford Youths | 4:5 pso | ||
| 18:00 | Sligo Rovers | - | Finn Harps | 4:1 | ||
| 18:00 | Drogheda United | - | Sporting Fingal | 0:2 | ||
| 19:45 | Bohemian FC | - | Shelbourne FC | 4:3 aet | ||
| 05/05/2009 | 19:45 | Athlone Town | - | UC Dublin | 0:1 |
