| 9. Ronde | 26.09.2009 | Coventry City | - | Middlesbrough FC | 2:2 |  |
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| 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 | |
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| 25. Ronde | 23.01.2010 | Middlesbrough FC | - | Swansea City | 1:1 | ||||
| 27. Ronde | 26.01.2010 | Doncaster Rovers | - | Middlesbrough FC | 1:4 | ||||
| 31. Ronde | 13.02.2010 | Middlesbrough FC | - | Peterborough United | 1:0 | ||||
| 39. Ronde | 23.03.2010 | Middlesbrough FC | - | Preston North End | 2:0 | ||||
| 45. Ronde | 24.04.2010 | Middlesbrough FC | - | Coventry City | 1:1 | ||||
| 46. Ronde | 02.05.2010 | Leicester City | - | Middlesbrough FC | 2:0 |
Engeland