| 2. Round | 13/03/2009 | Shamrock Rovers | - | Sligo Rovers | 2:1 |  |
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| 5. Round | 03/04/2009 | Drogheda United | - | Shamrock Rovers | 2:2 | |
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| 7. Round | 10/04/2009 | Shamrock Rovers | - | Cork City | 1:1 | |
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| 8. Round | 17/04/2009 | Galway United (old) | - | Shamrock Rovers | 1:3 | |
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| 9. Round | 25/04/2009 | Shamrock Rovers | - | St Patrick's Athletic | 2:0 | |
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| 12. Round | 16/05/2009 | Shamrock Rovers | - | Bohemian FC | 2:1 | |
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| 14. Round | 30/05/2009 | Shamrock Rovers | - | Drogheda United | 1:1 | |
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| 15. Round | 02/06/2009 | Shamrock Rovers | - | Dundalk FC | 3:1 | |
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| 18. Round | 04/07/2009 | St Patrick's Athletic | - | Shamrock Rovers | 1:2 | |
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| 19. Round | 10/07/2009 | Bray Wanderers | - | Shamrock Rovers | 1:2 | |
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| 23. Round | 07/08/2009 | Drogheda United | - | Shamrock Rovers | 0:1 | |
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| 25. Round | 22/08/2009 | Shamrock Rovers | - | Dundalk FC | 2:2 | |
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| 27. Round | 04/09/2009 | Shamrock Rovers | - | St Patrick's Athletic | 1:0 | |
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| 28. Round | 19/09/2009 | Shamrock Rovers | - | Bray Wanderers | 3:1 | |
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| 29. Round | 26/09/2009 | Sligo Rovers | - | Shamrock Rovers | 1:2 | |
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| 34. Round | 23/10/2009 | Dundalk FC | - | Shamrock Rovers | 2:4 | |
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| 35. Round | 30/10/2009 | Shamrock Rovers | - | Galway United (old) | 1:1 | |
Scotland