| 22. Round | 09/12/2008 | Wolverhampton Wanderers | - | Derby County | 3:0 | ||||
| 23. Round | 13/12/2008 | Wolverhampton Wanderers | - | Barnsley FC | 2:0 | ||||
| 24. Round | 20/12/2008 | Doncaster Rovers | - | Wolverhampton Wanderers | 0:1 | ||||
| 26. Round | 29/12/2008 | Blackpool FC | - | Wolverhampton Wanderers | 2:2 | ||||
| 28. Round | 17/01/2009 | Bristol City | - | Wolverhampton Wanderers | 2:2 | ||||
| 36. Round | 03/03/2009 | Crystal Palace | - | Wolverhampton Wanderers | 0:1 |  |
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| 37. Round | 07/03/2009 | Sheffield Wednesday | - | Wolverhampton Wanderers | 0:1 | |
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| 38. Round | 10/03/2009 | Wolverhampton Wanderers | - | Ipswich Town | 0:0 | ||||
| 39. Round | 14/03/2009 | Wolverhampton Wanderers | - | Charlton Athletic | 2:1 | ||||
| 40. Round | 21/03/2009 | Nottingham Forest | - | Wolverhampton Wanderers | 0:1 | ||||
| 41. Round | 06/04/2009 | Birmingham City | - | Wolverhampton Wanderers | 2:0 | ||||
| 42. Round | 10/04/2009 | Wolverhampton Wanderers | - | Southampton FC | 3:0 | ||||
| 43. Round | 13/04/2009 | Derby County | - | Wolverhampton Wanderers | 2:3 |
England