| ROUND | R3 | R4 | QF | SF | F | |||
| r3 | R | r4 | R | qf | R | |||
| Season archive |
| Tuesday, 9 June 2009 | ||||||
| r3 | Crumlin United | 1-1 | Shelbourne | |||
| Friday, 12 June 2009 | ||||||
| r3 | Bray Wanderers | 2-1 | Bluebell United | |||
| r3 | Blarney United | 0-2 | Sporting Fingal | |||
| r3 | Bohemians | 8-1 | Mayfield United | |||
| r3 | Cork City | 2-2 | Sligo Rovers | |||
| r3 | Derry City | 6-0 | Ballymun United | |||
| r3 | UCD | 3-1 | Arklow Town | |||
| r3 | Limerick | 0-1 | St. Patrick's | |||
| r3 | Mervue United | 1-3 | Dundalk | |||
| Saturday, 13 June 2009 | ||||||
| r3 | Shamrock Rovers | 1-1 | Drogheda United | |||
| r3 | Finn Harps | 0-3 | Galway United (old) | |||
| r3 | Kildare County | 1-2 | Athlone Town | |||
| r3 | Waterford | 6-0 | Carrigaline Utd | |||
| r3 | Tralee Dynamos | 2-1 | Salthill Devon | |||
| Sunday, 14 June 2009 | ||||||
| r3 | Wexford | 2-2 | Longford Town | |||
| r3 | Cherry Orchard | 2-2 | Monaghan United | |||
| Monday, 15 June 2009 | ||||||
| r3R | Shelbourne | 0-1 | Crumlin United | |||
| Tuesday, 16 June 2009 | ||||||
| r3R | Monaghan United | 4-0 | Cherry Orchard | |||
| r3R | Drogheda United | 0-3 | Shamrock Rovers | |||
| r3R | Sligo Rovers | 2-1 | Cork City | aet | ||
| Wednesday, 17 June 2009 | ||||||
| r3R | Longford Town | 3-2 | Wexford | aet | ||
| 3 | +3 | Aaron NASH (Derry City) |
| +3 | Raffael CRETARO (Sligo Rovers) | |
| +3 | Gavin DOYLE (Wexford, 2p) | |
| 2 | +2 | Glenn CROWE (Bohemians) |
| +2 | Graham CUMMINS (Waterford, 1p) | |
| +2 | Jason BYRNE (Bohemians) | |
| +2 | Wille-John KIELY (Waterford) | |
| +2 | Gary CURRAN (Longford Town) | |
| +2 | Tadhg PURCELL (Shamrock Rovers) | |
| +2 | Vinny FAHERTY (Galway United (old)) |