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