| 14. Round | 28/10/2008 | Sheffield Wednesday | - | Plymouth Argyle | 0:1 | ||||
| 21. Round | 06/12/2008 | Southampton FC | - | Sheffield Wednesday | 1:1 | ||||
| 22. Round | 09/12/2008 | Sheffield Wednesday | - | Queens Park Rangers | 1:0 | ||||
| 34. Round | 21/02/2009 | Sheffield Wednesday | - | Crystal Palace | 2:0 | ||||
| 39. Round | 14/03/2009 | Watford FC | - | Sheffield Wednesday | 2:2 | ||||
| 42. Round | 11/04/2009 | Sheffield Wednesday | - | Derby County | 0:1 |
USA