9. Round | 25/10/2008 | Blackburn Rovers | - | Middlesbrough FC | 1:1 | ||||
13. Round | 16/11/2008 | Everton FC | - | Middlesbrough FC | 1:1 | ||||
14. Round | 22/11/2008 | Middlesbrough FC | - | Bolton Wanderers | 1:3 | ||||
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 | ||||
20. Round | 29/12/2008 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
24. Round | 31/01/2009 | Middlesbrough FC | - | Blackburn Rovers | 0:0 | ||||
31. Round | 04/04/2009 | Bolton Wanderers | - | Middlesbrough FC | 4:1 | ||||
32. Round | 11/04/2009 | Middlesbrough FC | - | Hull City | 3:1 | ||||
34. Round | 26/04/2009 | Arsenal FC | - | Middlesbrough FC | 2:0 | ||||
35. Round | 02/05/2009 | Middlesbrough FC | - | Manchester United | 0:2 | ||||
36. Round | 11/05/2009 | Newcastle United | - | Middlesbrough FC | 3:1 | ||||
37. Round | 16/05/2009 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
38. Round | 24/05/2009 | West Ham United | - | Middlesbrough FC | 2:1 |