23. Round | 26/12/2009 | Middlesbrough FC | - | Scunthorpe United | 3:0 | ||||
24. Round | 28/12/2009 | Barnsley FC | - | Middlesbrough FC | 2:1 | ||||
26. Round | 16/01/2010 | Sheffield United | - | Middlesbrough FC | 1:0 | ||||
25. Round | 23/01/2010 | Middlesbrough FC | - | Swansea City | 1:1 | ||||
44. Round | 17/04/2010 | West Bromwich Albion | - | Middlesbrough FC | 2:0 | ||||
45. Round | 24/04/2010 | Middlesbrough FC | - | Coventry City | 1:1 |