| 17. Ronde | 13.12.2008 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
| 18. Ronde | 20.12.2008 | Fulham FC | - | Middlesbrough FC | 3:0 |  |
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| 19. Ronde | 26.12.2008 | Middlesbrough FC | - | Everton FC | 0:1 | |
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| 21. Ronde | 10.01.2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 22. Ronde | 17.01.2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
| 23. Ronde | 28.01.2009 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
| 29. Ronde | 14.03.2009 | Middlesbrough FC | - | Portsmouth FC | 1:1 | ||||
| 30. Ronde | 21.03.2009 | Stoke City | - | Middlesbrough FC | 1:0 | ||||
| 32. Ronde | 11.04.2009 | Middlesbrough FC | - | Hull City | 3:1 | ||||
| 33. Ronde | 18.04.2009 | Middlesbrough FC | - | Fulham FC | 0:0 | |
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| 34. Ronde | 26.04.2009 | Arsenal FC | - | Middlesbrough FC | 2:0 | ||||
| 35. Ronde | 02.05.2009 | Middlesbrough FC | - | Manchester United | 0:2 | ||||
| 38. Ronde | 24.05.2009 | West Ham United | - | Middlesbrough FC | 2:1 |
Engeland