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| 1st(1st leg) | Bohemian FC | - | Sligo Rovers | 0:0 | ||
| 2nd (2nd leg) | Sligo Rovers | - | Bohemian FC | 2:1 | ||
| 1st(1st leg): 11/09/2009 19:45 | 2nd (2nd leg): 15/09/2009 19:45 | Winner: Sligo Rovers | ||||
| 1st(1st leg) | Waterford United | - | St Patrick's Athletic | 1:1 | ||
| 2nd (2nd leg) | St Patrick's Athletic | - | Waterford United | 0:2 | ||
| 1st(1st leg): 12/09/2009 19:00 | 2nd (2nd leg): 15/09/2009 19:45 | Winner: Waterford United | ||||
| 1st(1st leg) | Longford Town | - | Bray Wanderers | 0:0 | ||
| 2nd (2nd leg) | Bray Wanderers | - | Longford Town | 2:1 | ||
| 1st(1st leg): 12/09/2009 19:30 | 2nd (2nd leg): 15/09/2009 19:45 | Winner: Bray Wanderers | ||||
| 1st(1st leg) | Sporting Fingal | - | Shamrock Rovers | 2:2 | ||
| 2nd (2nd leg) | Shamrock Rovers | - | Sporting Fingal | 1:2 aet | ||
| 1st(1st leg): 12/09/2009 19:30 | 2nd (2nd leg): 15/09/2009 20:00 | Winner: Sporting Fingal | ||||
