16. Round | 07/11/2009 | Crystal Palace | - | Middlesbrough FC | 1:0 | ||||
17. Round | 21/11/2009 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
18. Round | 28/11/2009 | Peterborough United | - | Middlesbrough FC | 2:2 | ||||
19. Round | 05/12/2009 | Queens Park Rangers | - | Middlesbrough FC | 1:5 | ||||
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 | ||||
23. Round | 26/12/2009 | Middlesbrough FC | - | Scunthorpe United | 3:0 | ||||
26. Round | 16/01/2010 | Sheffield United | - | Middlesbrough FC | 1:0 |