| 21. Round | 10/01/2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 24. Round | 31/01/2009 | Middlesbrough FC | - | Blackburn Rovers | 0:0 | ||||
| 26. Round | 21/02/2009 | Middlesbrough FC | - | Wigan Athletic | 0:0 | ||||
| 27. Round | 28/02/2009 | Middlesbrough FC | - | Liverpool FC | 2:0 | ||||
| 37. Round | 16/05/2009 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
| 38. Round | 24/05/2009 | West Ham United | - | Middlesbrough FC | 2:1 |
England