| 22. Ronde | 17.01.2009 | Bolton Wanderers | - | Manchester United | 0:1 |  |
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| 23. Ronde | 28.01.2009 | Blackburn Rovers | - | Bolton Wanderers | 2:2 | ||||
| 24. Ronde | 31.01.2009 | Bolton Wanderers | - | Tottenham Hotspur | 3:2 | ||||
| 25. Ronde | 07.02.2009 | Everton FC | - | Bolton Wanderers | 3:0 | ||||
| 28. Ronde | 04.03.2009 | Stoke City | - | Bolton Wanderers | 2:0 | ||||
| 37. Ronde | 16.05.2009 | Bolton Wanderers | - | Hull City | 1:1 |
Congo DR