| 14. Ronde | 28.10.2008 | Wolverhampton Wanderers | - | Swansea City | 2:1 | ||||
| 15. Ronde | 01.11.2008 | Cardiff City | - | Wolverhampton Wanderers | 1:2 | ||||
| 16. Ronde | 08.11.2008 | Wolverhampton Wanderers | - | Burnley FC | 2:0 | ||||
| 17. Ronde | 15.11.2008 | Southampton FC | - | Wolverhampton Wanderers | 1:2 |  |
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| 20. Ronde | 29.11.2008 | Wolverhampton Wanderers | - | Birmingham City | 1:1 | ||||
| 21. Ronde | 06.12.2008 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:0 | |
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| 22. Ronde | 09.12.2008 | Wolverhampton Wanderers | - | Derby County | 3:0 | ||||
| 23. Ronde | 13.12.2008 | Wolverhampton Wanderers | - | Barnsley FC | 2:0 | ||||
| 25. Ronde | 26.12.2008 | Wolverhampton Wanderers | - | Sheffield United | 1:1 | ||||
| 26. Ronde | 29.12.2008 | Blackpool FC | - | Wolverhampton Wanderers | 2:2 |
Engeland