| 29. Round | 01/02/2014 | Doncaster Rovers | - | Middlesbrough FC | 0:0 | ||||
| 32. Round | 22/02/2014 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
| 33. Round | 01/03/2014 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | ||||
| 34. Round | 08/03/2014 | Middlesbrough FC | - | Ipswich Town | 2:0 | ||||
| 35. Round | 11/03/2014 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 36. Round | 15/03/2014 | AFC Bournemouth | - | Middlesbrough FC | 0:0 |  |
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| 37. Round | 22/03/2014 | Middlesbrough FC | - | Queens Park Rangers | 1:3 | ||||
| 38. Round | 25/03/2014 | Huddersfield Town | - | Middlesbrough FC | 2:2 | ||||
| 39. Round | 29/03/2014 | Brighton & Hove Albion | - | Middlesbrough FC | 0:2 | ||||
| 40. Round | 05/04/2014 | Middlesbrough FC | - | Derby County | 1:0 | ||||
| 41. Round | 08/04/2014 | Middlesbrough FC | - | Birmingham City | 3:1 |  |
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| 43. Round | 19/04/2014 | Middlesbrough FC | - | Millwall FC | 1:2 | ||||
| 44. Round | 22/04/2014 | Reading FC | - | Middlesbrough FC | 2:0 | ||||
| 45. Round | 26/04/2014 | Middlesbrough FC | - | Barnsley FC | 3:1 |
Nigeria