| Round #20| 25.7.2008 | Cork City | St. Patrick's Athletic | - : - | | 25.7.2008 | Bohemians Dublin | UCD Dublin | - : - | | 25.7.2008 | Galway United | Derry City | - : - | | 25.7.2008 | Shamrock Rovers | Sligo Rovers | - : - | | 26.7.2008 | Cobh | Bray Wanderers | - : - | | 26.7.2008 | Finn Harps | Drogheda United | - : - |
Round #21| 1.8.2008 | Bohemians Dublin | Cobh | - : - | | 1.8.2008 | Derry City | Shamrock Rovers | - : - | | 1.8.2008 | Drogheda United | Bray Wanderers | - : - | | 1.8.2008 | UCD Dublin | St. Patrick's Athletic | - : - | | 1.8.2008 | Finn Harps | Galway United | - : - | | 2.8.2008 | Sligo Rovers | Cork City | - : - |
Round #22| 8.8.2008 | Bray Wanderers | Sligo Rovers | - : - | | 8.8.2008 | Cork City | Bohemians Dublin | - : - | | 8.8.2008 | Galway United | UCD Dublin | - : - | | 8.8.2008 | St. Patrick's Athletic | Drogheda United | - : - | | 8.8.2008 | Shamrock Rovers | Finn Harps | - : - | | 9.8.2008 | Cobh | Derry City | - : - |
Round #23| 22.8.2008 | Cork City | Bray Wanderers | - : - | | 22.8.2008 | Drogheda United | Shamrock Rovers | - : - | | 22.8.2008 | Galway United | Bohemians Dublin | - : - | | 22.8.2008 | St. Patrick's Athletic | Sligo Rovers | - : - | | 22.8.2008 | UCD Dublin | Derry City | - : - | | 22.8.2008 | Finn Harps | Cobh | - : - |
Round #24| 29.8.2008 | Bohemians Dublin | St. Patrick's Athletic | - : - | | 29.8.2008 | Bray Wanderers | UCD Dublin | - : - | | 29.8.2008 | Derry City | Finn Harps | - : - | | 29.8.2008 | Shamrock Rovers | Cork City | - : - | | 30.8.2008 | Cobh | Galway United | - : - | | 30.8.2008 | Sligo Rovers | Drogheda United | - : - |
Round #25| 5.9.2008 | Cork City | Derry City | - : - | | 5.9.2008 | Drogheda United | Cobh | - : - | | 5.9.2008 | St. Patrick's Athletic | Galway United | - : - | | 5.9.2008 | Finn Harps | UCD Dublin | - : - | | 5.9.2008 | Shamrock Rovers | Bray Wanderers | - : - | | 6.9.2008 | Sligo Rovers | Bohemians Dublin | - : - |
Round #26| 19.9.2008 | Bohemians Dublin | Finn Harps | - : - | | 19.9.2008 | Bray Wanderers | St. Patrick's Athletic | - : - | | 19.9.2008 | Derry City | Drogheda United | - : - | | 19.9.2008 | Galway United | Shamrock Rovers | - : - | | 19.9.2008 | UCD Dublin | Sligo Rovers | - : - | | 20.9.2008 | Cobh | Cork City | - : - |
Round #27| 26.9.2008 | Bray Wanderers | Finn Harps | - : - | | 26.9.2008 | Cork City | UCD Dublin | - : - | | 26.9.2008 | Drogheda United | Galway United | - : - | | 26.9.2008 | St. Patrick's Athletic | Derry City | - : - | | 26.9.2008 | Shamrock Rovers | Bohemians Dublin | - : - | | 27.9.2008 | Sligo Rovers | Cobh | - : - |
Round #28| 3.10.2008 | Bohemians Dublin | Bray Wanderers | - : - | | 3.10.2008 | Derry City | Sligo Rovers | - : - | | 3.10.2008 | Galway United | Cork City | - : - | | 3.10.2008 | UCD Dublin | Drogheda United | - : - | | 3.10.2008 | Finn Harps | St. Patrick's Athletic | - : - | | 4.10.2008 | Cobh | Shamrock Rovers | - : - |
Round #29| 10.10.2008 | Bray Wanderers | Derry City | - : - | | 10.10.2008 | Cork City | Finn Harps | - : - | | 10.10.2008 | Drogheda United | Bohemians Dublin | - : - | | 10.10.2008 | St. Patrick's Athletic | Cobh | - : - | | 10.10.2008 | Shamrock Rovers | UCD Dublin | - : - | | 11.10.2008 | Sligo Rovers | Galway United | - : - |
Round #30| 17.10.2008 | Bohemians Dublin | Derry City | - : - | | 17.10.2008 | Cork City | Drogheda United | - : - | | 17.10.2008 | Galway United | Bray Wanderers | - : - | | 17.10.2008 | Finn Harps | Sligo Rovers | - : - | | 17.10.2008 | Shamrock Rovers | St. Patrick's Athletic | - : - | | 18.10.2008 | Cobh | UCD Dublin | - : - |
Round #31| 31.10.2008 | Bray Wanderers | Cobh | - : - | | 31.10.2008 | Derry City | Galway United | - : - | | 31.10.2008 | St. Patrick's Athletic | Cork City | - : - | | 31.10.2008 | Drogheda United | Finn Harps | - : - | | 31.10.2008 | UCD Dublin | Bohemians Dublin | - : - | | 1.11.2008 | Sligo Rovers | Shamrock Rovers | - : - |
Round #32| 7.11.2008 | Bray Wanderers | Drogheda United | - : - | | 7.11.2008 | Cork City | Sligo Rovers | - : - | | 7.11.2008 | Galway United | Finn Harps | - : - | | 7.11.2008 | St. Patrick's Athletic | UCD Dublin | - : - | | 7.11.2008 | Shamrock Rovers | Derry City | - : - | | 8.11.2008 | Cobh | Bohemians Dublin | - : - |
Round #33| 14.11.2008 | Bohemians Dublin | Cork City | - : - | | 14.11.2008 | Derry City | Cobh | - : - | | 14.11.2008 | Drogheda United | St. Patrick's Athletic | - : - | | 14.11.2008 | Finn Harps | Shamrock Rovers | - : - | | 14.11.2008 | Sligo Rovers | Bray Wanderers | - : - | | 14.11.2008 | UCD Dublin | Galway United | - : - | |  Argentina 1 2
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