Round 25
|
| Friday, 5 September 2008 |
| Cork City - Derry City |
| Shamrock Rovers - Bray Wanderers |
| St.Patrick's - Galway United |
| Finn Harps - UCD |
| Drogheda United - Cobh Ramblers |
| Saturday, 6 September 2008 |
| Sligo Rovers - Bohemians |
Round 26
|
| Friday, 19 September 2008 |
| Bohemians - Finn Harps |
| UCD - Sligo Rovers |
| Derry City - Drogheda United |
| Bray Wanderers - St.Patrick's |
| Galway United - Shamrock Rovers |
| Saturday, 20 September 2008 |
| Cobh Ramblers - Cork City |
Round 27
|
| Friday, 26 September 2008 |
| Cork City - UCD |
| Shamrock Rovers - Bohemians |
| St.Patrick's - Derry City |
| Bray Wanderers - Finn Harps |
| Drogheda United - Galway United |
| Saturday, 27 September 2008 |
| Sligo Rovers - Cobh Ramblers |
Premier Division 2008