| 3. Jornada | 23.08.2008 | Sheffield Wednesday | - | Preston North End | 1:1 | ||||
| 4. Jornada | 30.08.2008 | Swansea City | - | Sheffield Wednesday | 1:1 |  |
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| 5. Jornada | 13.09.2008 | Sheffield Wednesday | - | Watford FC | 2:0 | ||||
| 6. Jornada | 16.09.2008 | Reading | - | Sheffield Wednesday | 6:0 | ||||
| 7. Jornada | 20.09.2008 | Sheffield Wednesday | - | Ipswich Town | 0:0 | ||||
| 8. Jornada | 27.09.2008 | Charlton Athletic | - | Sheffield Wednesday | 1:2 | |
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| 9. Jornada | 30.09.2008 | Sheffield Wednesday | - | Nottingham Forest | 1:0 | ||||
| 10. Jornada | 04.10.2008 | Plymouth Argyle | - | Sheffield Wednesday | 4:0 | ||||
| 11. Jornada | 19.10.2008 | Sheffield Wednesday | - | Sheffield United | 1:0 | ||||
| 12. Jornada | 21.10.2008 | Barnsley FC | - | Sheffield Wednesday | 2:1 |  |
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| 16. Jornada | 08.11.2008 | Sheffield Wednesday | - | Doncaster Rovers | 1:0 | ||||
| 17. Jornada | 15.11.2008 | Derby County | - | Sheffield Wednesday | 3:0 | ||||
| 18. Jornada | 22.11.2008 | Sheffield Wednesday | - | Coventry City | 0:1 | ||||
| 19. Jornada | 25.11.2008 | Blackpool FC | - | Sheffield Wednesday | 0:2 | ||||
| 20. Jornada | 29.11.2008 | Sheffield Wednesday | - | Norwich City | 3:2 |  |
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Inglaterra