| 1. Round | 15/08/2009 | Wolverhampton Wanderers | - | West Ham United | 0:2 | ||||
| 2. Round | 18/08/2009 | Wigan Athletic | - | Wolverhampton Wanderers | 0:1 | ||||
| 3. Round | 22/08/2009 | Manchester City | - | Wolverhampton Wanderers | 1:0 | ||||
| 4. Round | 29/08/2009 | Wolverhampton Wanderers | - | Hull City | 1:1 | ||||
| 5. Round | 12/09/2009 | Blackburn Rovers | - | Wolverhampton Wanderers | 3:1 | ||||
| 6. Round | 20/09/2009 | Wolverhampton Wanderers | - | Fulham FC | 2:1 | ||||
| 7. Round | 27/09/2009 | Sunderland AFC | - | Wolverhampton Wanderers | 5:2 | ||||
| 8. Round | 03/10/2009 | Wolverhampton Wanderers | - | Portsmouth FC | 0:1 | ||||
| 9. Round | 17/10/2009 | Everton FC | - | Wolverhampton Wanderers | 1:1 | ||||
| 10. Round | 24/10/2009 | Wolverhampton Wanderers | - | Aston Villa | 1:1 | ||||
| 11. Round | 31/10/2009 | Stoke City | - | Wolverhampton Wanderers | 2:2 | ||||
| 12. Round | 07/11/2009 | Wolverhampton Wanderers | - | Arsenal FC | 1:4 | ||||
| 13. Round | 21/11/2009 | Chelsea FC | - | Wolverhampton Wanderers | 4:0 |
Wales
