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| 06.06.2008 | 20:30 | Bohemian FC | - | Drogheda Town | 3:0 | |
| 20:45 | Galway United (old) | - | Waterford United | 1:0 | ||
| 20:45 | Douglas Hall | - | Drogheda United | 0:3 | ||
| 20:45 | Limerick 37 FC | - | Cork City | 0:2 | ||
| 20:45 | St Patrick's Athletic | - | Longford Town | 2:1 | ||
| 20:45 | Athlone Town | - | Finn Harps | 2:1 | ||
| 20:45 | Derry City | - | Liffeys Pearse FC | 2:0 | ||
| 20:45 | Sporting Fingal | - | Cobh Ramblers | 2:0 | ||
| 21:00 | Wexford Youths | - | Killester United | 0:0 | ||
| 21:00 | Shelbourne FC | - | Dundalk FC | 0:3 | ||
| 21:00 | Monaghan United | - | UC Dublin | 0:0 | ||
| 07.06.2008 | 18:00 | St. Mary's AFC | - | Wayside Celtic | 0:1 | |
| 20:30 | Shamrock Rovers | - | Sligo Rovers | 2:1 | ||
| 08.06.2008 | 13:00 | Everton AFC | - | Carrick United | 0:2 | |
| 15:00 | Rockmount AFC | - | Bray Wanderers | 0:3 | ||
| 24.06.2008 | 19:00 | Kildare County | - | Fanad United | 3:0 | |
| Partidos decisivos | ||||||
|---|---|---|---|---|---|---|
| 18:45 | Killester United | - | Wexford Youths | 1:2 | ||
| 20:45 | UC Dublin | - | Monaghan United | 0:1 | ||
