| 15. Ronde | 31.10.2009 | Middlesbrough FC | - | Plymouth Argyle | 0:1 | ||||
| 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 |  |
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| 21. Ronde | 13.12.2009 | Middlesbrough FC | - | Cardiff City | 0:1 | ||||
| 22. Ronde | 20.12.2009 | Newcastle United | - | Middlesbrough FC | 2:0 | |
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| 23. Ronde | 26.12.2009 | Middlesbrough FC | - | Scunthorpe United | 3:0 | ||||
| 30. Ronde | 09.02.2010 | Middlesbrough FC | - | Barnsley FC | 2:1 | ||||
| 33. Ronde | 20.02.2010 | Nottingham Forest | - | Middlesbrough FC | 1:0 | ||||
| 34. Ronde | 27.02.2010 | Middlesbrough FC | - | Queens Park Rangers | 2:0 | ||||
| 38. Ronde | 20.03.2010 | Middlesbrough FC | - | Reading FC | 1:1 | ||||
| 39. Ronde | 23.03.2010 | Middlesbrough FC | - | Preston North End | 2:0 |
Oostenrijk