| 7. Journée | 15.09.2009 | Sheffield Wednesday | - | Middlesbrough FC | 1:3 | ||||
| 8. Journée | 19.09.2009 | Middlesbrough FC | - | West Bromwich Albion | 0:5 | ||||
| 9. Journée | 26.09.2009 | Coventry City | - | Middlesbrough FC | 2:2 |  |
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| 10. Journée | 29.09.2009 | Middlesbrough FC | - | Leicester City | 0:1 | ||||
| 11. Journée | 03.10.2009 | Reading FC | - | Middlesbrough FC | 0:2 | |
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| 12. Journée | 17.10.2009 | Middlesbrough FC | - | Watford FC | 0:1 | ||||
| 13. Journée | 20.10.2009 | Middlesbrough FC | - | Derby County | 2:0 | ||||
| 14. Journée | 24.10.2009 | Preston North End | - | Middlesbrough FC | 2:2 | ||||
| 15. Journée | 31.10.2009 | Middlesbrough FC | - | Plymouth Argyle | 0:1 | ||||
| 16. Journée | 07.11.2009 | Crystal Palace | - | Middlesbrough FC | 1:0 | ||||
| 17. Journée | 21.11.2009 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 18. Journée | 28.11.2009 | Peterborough United | - | Middlesbrough FC | 2:2 | ||||
| 19. Journée | 05.12.2009 | Queens Park Rangers | - | Middlesbrough FC | 1:5 | ||||
| 20. Journée | 08.12.2009 | Middlesbrough FC | - | Blackpool FC | 0:3 | ||||
| 21. Journée | 13.12.2009 | Middlesbrough FC | - | Cardiff City | 0:1 |
Angleterre