| 20. Jornada | 29.12.2008 | Manchester United | - | Middlesbrough | 1:0 | ||||
| 21. Jornada | 10.01.2009 | Middlesbrough | - | Sunderland | 1:1 | ||||
| 22. Jornada | 17.01.2009 | West Bromwich Albion | - | Middlesbrough | 3:0 | ||||
| 23. Jornada | 28.01.2009 | Chelsea | - | Middlesbrough | 2:0 | ||||
| 24. Jornada | 31.01.2009 | Middlesbrough | - | Blackburn Rovers | 0:0 | ||||
| 25. Jornada | 07.02.2009 | Manchester City | - | Middlesbrough | 1:0 | ||||
| 27. Jornada | 28.02.2009 | Middlesbrough | - | Liverpool | 2:0 |  |
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| 28. Jornada | 04.03.2009 | Tottenham Hotspur | - | Middlesbrough | 4:0 | ||||
| 29. Jornada | 14.03.2009 | Middlesbrough | - | Portsmouth FC | 1:1 |  |
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| 31. Jornada | 04.04.2009 | Bolton Wanderers | - | Middlesbrough | 4:1 | ||||
| 32. Jornada | 11.04.2009 | Middlesbrough | - | Hull City | 3:1 |  |
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| 33. Jornada | 18.04.2009 | Middlesbrough | - | Fulham FC | 0:0 | ||||
| 34. Jornada | 26.04.2009 | Arsenal | - | Middlesbrough | 2:0 | ||||
| 35. Jornada | 02.05.2009 | Middlesbrough | - | Manchester United | 0:2 | ||||
| 36. Jornada | 11.05.2009 | Newcastle United | - | Middlesbrough | 3:1 | |
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| 37. Jornada | 16.05.2009 | Middlesbrough | - | Aston Villa | 1:1 | ||||
| 38. Jornada | 24.05.2009 | West Ham United | - | Middlesbrough | 2:1 |
Inglaterra