| 4. Ronde | 27.03.2009 | Cork City | - | Bray Wanderers | 2:1 |  |
|||
| 14. Ronde | 29.05.2009 | St Patrick's Athletic | - | Bray Wanderers | 1:1 | |
 |
||
| 19. Ronde | 10.07.2009 | Bray Wanderers | - | Shamrock Rovers | 1:2 | |
|||
| 31. Ronde | 09.10.2009 | Bray Wanderers | - | Cork City | 3:2 | |
|||
| 35. Ronde | 30.10.2009 | Derry City | - | Bray Wanderers | 3:0 |
Ierland