| ROUND | R1 | R2 | QF | SF | F |
| Season archive |
| Monday, 13 April 2009 | ||||||
| r1 | Shamrock Rovers | 3-0 | Kildare County | |||
| 44 | Purcell | |||||
| 47(og) | ||||||
| 67(p) | Bradley | |||||
| r1 | Monaghan United | 1-2 | Sporting Fingal | |||
| 73 | 11 | Byrne | ||||
| 27 | Byrne | |||||
| r1 | Limerick | 1-1 | Wexford | aet, p3-5 | ||
| 81 | 47 | |||||
| r1 | FC Carlow | 3-2 | Cobh Ramblers | |||
| 4 | 25 | |||||
| 75 | 80 | |||||
| 83 | ||||||
| r1 | Bray Wanderers | 0-2 | Drogheda United | |||
| 57 | King | |||||
| 86 | Chambers | |||||
| r1 | Galway United (old) | 2-2 | Salthill Devon | aet, p5-3 | ||
| 8 | O'Shea | 72 | ||||
| 26 | Edwards | 78 | ||||
| r1 | Shelbourne | 3-0 | Dundalk | |||
| 27 | Hynes | |||||
| 32 | Baker | |||||
| 76 | Madden | |||||
| Tuesday, 14 April 2009 | ||||||
| r1 | Tullamore Town | 0-2 | UCD | |||
| 35 | McMahon | |||||
| 40 | Purcell | |||||
| r1 | Athlone Town | 3-0 | Longford Town | |||
| 22 | Onwubiko | |||||
| 63 | ||||||
| 89 | Onwubiko | |||||
| r1 | Castlebar Celtic | 0-4 | Finn Harps | |||
| 59 | Funston | |||||
| 72 | McDaid | |||||
| 74 | ||||||
| 90 | ||||||
| r1 | Kerry League | 1-3 | Cork City | aet | ||
| 64 | 34 | Kiely | ||||
| 91 | Murphy | |||||
| 115 | Behan | |||||
| 2 | +2 | Conan BYRNE (Sporting Fingal) |
| +2 | Emeka ONWUBIKO (Athlone Town) | |
| 1 | +1 | Peter McMAHON (UCD) |
| +1 | James CHAMBERS (Drogheda United) | |
| +1 | Timmy PURCELL (UCD) | |
| +1 | Michael FUNSTON (Finn Harps) | |
| +1 | David McDAID (Finn Harps) | |
| +1 | Peter HYNES (Shelbourne) | |
| +1 | Brian KING (Drogheda United) | |
| +1 | Dennis BEHAN (Cork City) | |
| +1 | Tim KIELY (Cork City) | |
| +1 | Paddy MADDEN (Shelbourne) | |
| +1 | Declan EDWARDS (Galway United (old)) | |
| +1 | Stephen BRADLEY (Shamrock Rovers, 1p) | |
| +1 | Jay O'SHEA (Galway United (old)) | |
| +1 | Tadhg PURCELL (Shamrock Rovers) | |
| +1 | Daniel MURPHY (Cork City) | |
| +1 | Richie BAKER (Shelbourne) |