| 29. Round | 06/02/2010 | Ipswich Town | - | Middlesbrough FC | 1:1 | ||||
| 30. Round | 09/02/2010 | Middlesbrough FC | - | Barnsley FC | 2:1 | ||||
| 31. Round | 13/02/2010 | Middlesbrough FC | - | Peterborough United | 1:0 | ||||
| 32. Round | 16/02/2010 | Blackpool FC | - | Middlesbrough FC | 2:0 | ||||
| 36. Round | 13/03/2010 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
| 37. Round | 16/03/2010 | Derby County | - | Middlesbrough FC | 2:2 | ||||
| 39. Round | 23/03/2010 | Middlesbrough FC | - | Preston North End | 2:0 | ||||
| 40. Round | 27/03/2010 | Watford FC | - | Middlesbrough FC | 1:1 | ||||
| 42. Round | 05/04/2010 | Plymouth Argyle | - | Middlesbrough FC | 0:2 | ||||
| 45. Round | 24/04/2010 | Middlesbrough FC | - | Coventry City | 1:1 |
Scotland