| 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 | ||||
| 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 | |
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| 25. Round | 23/01/2010 | Middlesbrough FC | - | Swansea City | 1:1 | ||||
| 27. Round | 26/01/2010 | Doncaster Rovers | - | Middlesbrough FC | 1:4 | ||||
| 31. Round | 13/02/2010 | Middlesbrough FC | - | Peterborough United | 1:0 | ||||
| 39. Round | 23/03/2010 | Middlesbrough FC | - | Preston North End | 2:0 | ||||
| 45. Round | 24/04/2010 | Middlesbrough FC | - | Coventry City | 1:1 | ||||
| 46. Round | 02/05/2010 | Leicester City | - | Middlesbrough FC | 2:0 |
England
