| 21. Jornada | 10.01.2009 | Middlesbrough | - | Sunderland | 1:1 | ||||
| 24. Jornada | 31.01.2009 | Middlesbrough | - | Blackburn Rovers | 0:0 | ||||
| 26. Jornada | 21.02.2009 | Middlesbrough | - | Wigan Athletic | 0:0 | ||||
| 27. Jornada | 28.02.2009 | Middlesbrough | - | Liverpool | 2:0 | ||||
| 37. Jornada | 16.05.2009 | Middlesbrough | - | Aston Villa | 1:1 | ||||
| 38. Jornada | 24.05.2009 | West Ham United | - | Middlesbrough | 2:1 |
Inglaterra