| 3. Round | 22/08/2009 | Hull City | - | Bolton Wanderers | 1:0 | ||||
| 5. Round | 12/09/2009 | Portsmouth FC | - | Bolton Wanderers | 2:3 | ||||
| 8. Round | 03/10/2009 | Bolton Wanderers | - | Tottenham Hotspur | 2:2 | ||||
| 9. Round | 17/10/2009 | Manchester United | - | Bolton Wanderers | 2:1 | ||||
| 11. Round | 31/10/2009 | Bolton Wanderers | - | Chelsea FC | 0:4 | ||||
| 13. Round | 22/11/2009 | Bolton Wanderers | - | Blackburn Rovers | 0:2 | ||||
| 14. Round | 28/11/2009 | Fulham FC | - | Bolton Wanderers | 1:1 | ||||
| 16. Round | 12/12/2009 | Bolton Wanderers | - | Manchester City | 3:3 | ||||
| 19. Round | 26/12/2009 | Burnley FC | - | Bolton Wanderers | 1:1 | ||||
| 2. Round | 20/01/2010 | Arsenal FC | - | Bolton Wanderers | 4:2 | ||||
| 24. Round | 30/01/2010 | Liverpool FC | - | Bolton Wanderers | 2:0 |  |
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| 25. Round | 06/02/2010 | Bolton Wanderers | - | Fulham FC | 0:0 | ||||
| 26. Round | 09/02/2010 | Manchester City | - | Bolton Wanderers | 2:0 | ||||
| 27. Round | 21/02/2010 | Blackburn Rovers | - | Bolton Wanderers | 3:0 | ||||
| 31. Round | 20/03/2010 | Everton FC | - | Bolton Wanderers | 2:0 | ||||
| 35. Round | 17/04/2010 | Stoke City | - | Bolton Wanderers | 1:2 | ||||
| 36. Round | 24/04/2010 | Bolton Wanderers | - | Portsmouth FC | 2:2 |
England
