| 4. Round | 13/09/2008 | Portsmouth FC | - | Middlesbrough FC | 2:1 | ||||
| 7. Round | 04/10/2008 | Wigan Athletic | - | Middlesbrough FC | 0:1 | ||||
| 8. Round | 18/10/2008 | Middlesbrough FC | - | Chelsea FC | 0:5 | ||||
| 9. Round | 25/10/2008 | Blackburn Rovers | - | Middlesbrough FC | 1:1 | ||||
| 10. Round | 29/10/2008 | Middlesbrough FC | - | Manchester City | 2:0 | ||||
| 11. Round | 01/11/2008 | Middlesbrough FC | - | West Ham United | 1:1 |  |
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| 12. Round | 09/11/2008 | Aston Villa | - | Middlesbrough FC | 1:2 | ||||
| 13. Round | 16/11/2008 | Everton FC | - | Middlesbrough FC | 1:1 | ||||
| 17. Round | 13/12/2008 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
| 18. Round | 20/12/2008 | Fulham FC | - | Middlesbrough FC | 3:0 | ||||
| 19. Round | 26/12/2008 | Middlesbrough FC | - | Everton FC | 0:1 | |
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| 20. Round | 29/12/2008 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
| 21. Round | 10/01/2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 22. Round | 17/01/2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
| 23. Round | 28/01/2009 | Chelsea FC | - | Middlesbrough FC | 2:0 | |
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| 24. Round | 31/01/2009 | Middlesbrough FC | - | Blackburn Rovers | 0:0 | ||||
| 25. Round | 07/02/2009 | Manchester City | - | Middlesbrough FC | 1:0 |
England