| 7. Round | 15/09/2009 | Sheffield Wednesday | - | Middlesbrough FC | 1:3 | ||||
| 8. Round | 19/09/2009 | Middlesbrough FC | - | West Bromwich Albion | 0:5 | ||||
| 9. Round | 26/09/2009 | Coventry City | - | Middlesbrough FC | 2:2 |  |
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| 10. Round | 29/09/2009 | Middlesbrough FC | - | Leicester City | 0:1 | ||||
| 11. Round | 03/10/2009 | Reading FC | - | Middlesbrough FC | 0:2 | |
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| 12. Round | 17/10/2009 | Middlesbrough FC | - | Watford FC | 0:1 | ||||
| 13. Round | 20/10/2009 | Middlesbrough FC | - | Derby County | 2:0 | ||||
| 14. Round | 24/10/2009 | Preston North End | - | Middlesbrough FC | 2:2 | ||||
| 15. Round | 31/10/2009 | Middlesbrough FC | - | Plymouth Argyle | 0:1 | ||||
| 16. Round | 07/11/2009 | Crystal Palace | - | Middlesbrough FC | 1:0 | ||||
| 17. Round | 21/11/2009 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 18. Round | 28/11/2009 | Peterborough United | - | Middlesbrough FC | 2:2 | ||||
| 19. Round | 05/12/2009 | Queens Park Rangers | - | Middlesbrough FC | 1:5 | ||||
| 20. Round | 08/12/2009 | Middlesbrough FC | - | Blackpool FC | 0:3 | ||||
| 21. Round | 13/12/2009 | Middlesbrough FC | - | Cardiff City | 0:1 |
England