21. Round | 24/07/2009 | Dundalk FC | - | Drogheda United | 4:2 | ||||
22. Round | 31/07/2009 | Drogheda United | - | Bohemian FC | 1:1 | ||||
27. Round | 04/09/2009 | Drogheda United | - | Sligo Rovers | 2:2 | ||||
29. Round | 25/09/2009 | Bray Wanderers | - | Drogheda United | 1:2 | ||||
30. Round | 02/10/2009 | Drogheda United | - | Dundalk FC | 2:2 | ||||
35. Round | 30/10/2009 | Drogheda United | - | St Patrick's Athletic | 1:2 |