| 4. Round | 30/08/2008 | Wolverhampton Wanderers | - | Nottingham Forest | 5:1 | ||||
| 5. Round | 13/09/2008 | Charlton Athletic | - | Wolverhampton Wanderers | 1:3 | ||||
| 6. Round | 16/09/2008 | Wolverhampton Wanderers | - | Crystal Palace | 2:1 | ||||
| 8. Round | 27/09/2008 | Wolverhampton Wanderers | - | Bristol City | 2:0 | ||||
| 13. Round | 25/10/2008 | Watford FC | - | Wolverhampton Wanderers | 2:3 |  |
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| 15. Round | 01/11/2008 | Cardiff City | - | Wolverhampton Wanderers | 1:2 | ||||
| 18. Round | 22/11/2008 | Wolverhampton Wanderers | - | Blackpool FC | 2:0 | ||||
| 20. Round | 29/11/2008 | Wolverhampton Wanderers | - | Birmingham City | 1:1 |
England