| 17. Round | 21/11/2009 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 18. Round | 28/11/2009 | Peterborough United | - | Middlesbrough FC | 2:2 |  |
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| 19. Round | 05/12/2009 | Queens Park Rangers | - | Middlesbrough FC | 1:5 | |
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| 20. Round | 08/12/2009 | Middlesbrough FC | - | Blackpool FC | 0:3 | ||||
| 21. Round | 13/12/2009 | Middlesbrough FC | - | Cardiff City | 0:1 | ||||
| 22. Round | 20/12/2009 | Newcastle United | - | Middlesbrough FC | 2:0 |
England