| 2. Ronde | 13.03.2009 | Shamrock Rovers | - | Sligo Rovers | 2:1 |  |
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| 5. Ronde | 03.04.2009 | Drogheda United | - | Shamrock Rovers | 2:2 | |
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| 7. Ronde | 10.04.2009 | Shamrock Rovers | - | Cork City | 1:1 | |
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| 8. Ronde | 17.04.2009 | Galway United (old) | - | Shamrock Rovers | 1:3 | |
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| 9. Ronde | 25.04.2009 | Shamrock Rovers | - | St Patrick's Athletic | 2:0 | |
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| 12. Ronde | 16.05.2009 | Shamrock Rovers | - | Bohemian FC | 2:1 | |
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| 14. Ronde | 30.05.2009 | Shamrock Rovers | - | Drogheda United | 1:1 | |
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| 15. Ronde | 02.06.2009 | Shamrock Rovers | - | Dundalk FC | 3:1 | |
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| 18. Ronde | 04.07.2009 | St Patrick's Athletic | - | Shamrock Rovers | 1:2 | |
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| 19. Ronde | 10.07.2009 | Bray Wanderers | - | Shamrock Rovers | 1:2 | |
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| 23. Ronde | 07.08.2009 | Drogheda United | - | Shamrock Rovers | 0:1 | |
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| 25. Ronde | 22.08.2009 | Shamrock Rovers | - | Dundalk FC | 2:2 | |
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| 27. Ronde | 04.09.2009 | Shamrock Rovers | - | St Patrick's Athletic | 1:0 | |
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| 28. Ronde | 19.09.2009 | Shamrock Rovers | - | Bray Wanderers | 3:1 | |
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| 29. Ronde | 26.09.2009 | Sligo Rovers | - | Shamrock Rovers | 1:2 | |
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| 34. Ronde | 23.10.2009 | Dundalk FC | - | Shamrock Rovers | 2:4 | |
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| 35. Ronde | 30.10.2009 | Shamrock Rovers | - | Galway United (old) | 1:1 | |
Schotland