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| 09/06/2009 | 20:00 | Crumlin United | - | Shelbourne FC | 1:1 | |
| 12/06/2009 | 19:45 | Mervue United | - | Dundalk FC | 1:3 | |
| 19:45 | Blarney United | - | Sporting Fingal | 0:2 | ||
| 19:45 | Bray Wanderers | - | Bluebell United | 2:1 | ||
| 19:45 | Limerick 37 FC | - | St Patrick's Athletic | 0:1 | ||
| 19:45 | Derry City | - | Ballymun United | 6:0 | ||
| 19:45 | UC Dublin | - | Arklow Town | 3:1 | ||
| 19:45 | Bohemian FC | - | Mayfield United | 8:1 | ||
| 19:45 | Cork City | - | Sligo Rovers | 2:2 | ||
| 13/06/2009 | 18:30 | Tralee Dynamos | - | Salthill Devon | 2:1 | |
| 19:00 | Shamrock Rovers | - | Drogheda United | 1:1 | ||
| 19:00 | Waterford United | - | Carrigaline United | 6:0 | ||
| 19:30 | Kildare County | - | Athlone Town | 1:2 | ||
| 19:45 | Finn Harps | - | Galway United (old) | 0:3 | ||
| 14/06/2009 | 15:00 | Cherry Orchard | - | Monaghan United | 2:2 | |
| 18:00 | Wexford Youths | - | Longford Town | 2:2 | ||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 15/06/2009 | 20:00 | Shelbourne FC | - | Crumlin United | 0:1 | |
| 16/06/2009 | 19:45 | Sligo Rovers | - | Cork City | 2:1 aet | |
| 19:45 | Drogheda United | - | Shamrock Rovers | 0:3 | ||
| 20:00 | Monaghan United | - | Cherry Orchard | 4:0 | ||
| 17/06/2009 | 18:00 | Longford Town | - | Wexford Youths | 3:2 aet | |
