| 23. Round | 28/01/2009 | West Ham United | - | Hull City | 2:0 | ||||
| 24. Round | 31/01/2009 | Arsenal FC | - | West Ham United | 0:0 | ||||
| 25. Round | 08/02/2009 | West Ham United | - | Manchester United | 0:1 | ||||
| 26. Round | 21/02/2009 | Bolton Wanderers | - | West Ham United | 2:1 | ||||
| 27. Round | 01/03/2009 | West Ham United | - | Manchester City | 1:0 | ||||
| 28. Round | 04/03/2009 | Wigan Athletic | - | West Ham United | 0:1 |  |
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| 29. Round | 16/03/2009 | West Ham United | - | West Bromwich Albion | 0:0 | |
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| 32. Round | 11/04/2009 | Tottenham Hotspur | - | West Ham United | 1:0 | ||||
| 33. Round | 18/04/2009 | Aston Villa | - | West Ham United | 1:1 | ||||
| 34. Round | 25/04/2009 | West Ham United | - | Chelsea FC | 0:1 |
Uganda