| 6. Round | 27/09/2008 | Middlesbrough FC | - | West Bromwich Albion | 0:1 | ||||
| 7. Round | 04/10/2008 | West Bromwich Albion | - | Fulham FC | 1:0 | ||||
| 8. Round | 18/10/2008 | Manchester United | - | West Bromwich Albion | 4:0 | ||||
| 9. Round | 25/10/2008 | West Bromwich Albion | - | Hull City | 0:3 | ||||
| 10. Round | 28/10/2008 | Newcastle United | - | West Bromwich Albion | 2:1 |  |
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| 11. Round | 01/11/2008 | West Bromwich Albion | - | Blackburn Rovers | 2:2 | |
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| 12. Round | 08/11/2008 | Liverpool FC | - | West Bromwich Albion | 3:0 | ||||
| 13. Round | 15/11/2008 | West Bromwich Albion | - | Chelsea FC | 0:3 | ||||
| 22. Round | 17/01/2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
| 23. Round | 27/01/2009 | West Bromwich Albion | - | Manchester United | 0:5 | |
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| 24. Round | 31/01/2009 | Hull City | - | West Bromwich Albion | 2:2 | ||||
| 27. Round | 28/02/2009 | Everton FC | - | West Bromwich Albion | 2:0 | ||||
| 28. Round | 03/03/2009 | West Bromwich Albion | - | Arsenal FC | 1:3 | |
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| 36. Round | 09/05/2009 | West Bromwich Albion | - | Wigan Athletic | 3:1 | ||||
| 37. Round | 17/05/2009 | West Bromwich Albion | - | Liverpool FC | 0:2 | ||||
| 38. Round | 24/05/2009 | Blackburn Rovers | - | West Bromwich Albion | 0:0 |
Netherlands