| 4. Jornada | 13.09.2008 | Portsmouth FC | - | Middlesbrough | 2:1 | ||||
| 7. Jornada | 04.10.2008 | Wigan Athletic | - | Middlesbrough | 0:1 | ||||
| 8. Jornada | 18.10.2008 | Middlesbrough | - | Chelsea | 0:5 | ||||
| 9. Jornada | 25.10.2008 | Blackburn Rovers | - | Middlesbrough | 1:1 | ||||
| 10. Jornada | 29.10.2008 | Middlesbrough | - | Manchester City | 2:0 | ||||
| 11. Jornada | 01.11.2008 | Middlesbrough | - | West Ham United | 1:1 |  |
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| 12. Jornada | 09.11.2008 | Aston Villa | - | Middlesbrough | 1:2 | ||||
| 13. Jornada | 16.11.2008 | Everton | - | Middlesbrough | 1:1 | ||||
| 17. Jornada | 13.12.2008 | Middlesbrough | - | Arsenal | 1:1 | ||||
| 18. Jornada | 20.12.2008 | Fulham FC | - | Middlesbrough | 3:0 | ||||
| 19. Jornada | 26.12.2008 | Middlesbrough | - | Everton | 0:1 | |
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| 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 | |
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| 24. Jornada | 31.01.2009 | Middlesbrough | - | Blackburn Rovers | 0:0 | ||||
| 25. Jornada | 07.02.2009 | Manchester City | - | Middlesbrough | 1:0 |
Inglaterra