Round 28
|
| Friday, 3 October 2008 |
| Bohemians - Bray Wanderers |
| UCD - Drogheda United |
| Finn Harps - St.Patrick's |
| Derry City - Sligo Rovers |
| Galway United - Cork City |
| Saturday, 4 October 2008 |
| Cobh Ramblers - Shamrock Rovers |
Round 29
|
| Friday, 10 October 2008 |
| Cork City - Finn Harps |
| Shamrock Rovers - UCD |
| St.Patrick's - Cobh Ramblers |
| Bray Wanderers - Derry City |
| Drogheda United - Bohemians |
| Saturday, 11 October 2008 |
| Sligo Rovers - Galway United |
Round 30
|
| Friday, 17 October 2008 |
| Cork City - Drogheda United |
| Shamrock Rovers - St.Patrick's |
| Bohemians - Derry City |
| Finn Harps - Sligo Rovers |
| Galway United - Bray Wanderers |
| Saturday, 18 October 2008 |
| Cobh Ramblers - UCD |
Round 31
|
| Friday, 31 October 2008 |
| St.Patrick's - Cork City |
| UCD - Bohemians |
| Derry City - Galway United |
| Bray Wanderers - Cobh Ramblers |
| Drogheda United - Finn Harps |
Premier Division 2008