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| H (Match allé) | Bohemian FC | - | Sligo Rovers | 0:0 | ||
| R (match retour) | Sligo Rovers | - | Bohemian FC | 2:1 | ||
| H (Match allé): 11.09.2009 20:45 | R (match retour): 15.09.2009 20:45 | vainqueur: Sligo Rovers | ||||
| H (Match allé) | Waterford United | - | St Patrick's Athletic | 1:1 | ||
| R (match retour) | St Patrick's Athletic | - | Waterford United | 0:2 | ||
| H (Match allé): 12.09.2009 20:00 | R (match retour): 15.09.2009 20:45 | vainqueur: Waterford United | ||||
| H (Match allé) | Longford Town | - | Bray Wanderers | 0:0 | ||
| R (match retour) | Bray Wanderers | - | Longford Town | 2:1 | ||
| H (Match allé): 12.09.2009 20:30 | R (match retour): 15.09.2009 20:45 | vainqueur: Bray Wanderers | ||||
| H (Match allé) | Sporting Fingal | - | Shamrock Rovers | 2:2 | ||
| R (match retour) | Shamrock Rovers | - | Sporting Fingal | 1:2 ap | ||
| H (Match allé): 12.09.2009 20:30 | R (match retour): 15.09.2009 21:00 | vainqueur: Sporting Fingal | ||||
