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 | ||||
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 | ||||
29. Round | 14/03/2009 | Middlesbrough FC | - | Portsmouth FC | 1:1 | ||||
30. Round | 21/03/2009 | Stoke City | - | Middlesbrough FC | 1:0 | ||||
32. Round | 11/04/2009 | Middlesbrough FC | - | Hull City | 3:1 | ||||
33. Round | 18/04/2009 | Middlesbrough FC | - | Fulham FC | 0:0 | ||||
34. Round | 26/04/2009 | Arsenal FC | - | Middlesbrough FC | 2:0 | ||||
35. Round | 02/05/2009 | Middlesbrough FC | - | Manchester United | 0:2 | ||||
38. Round | 24/05/2009 | West Ham United | - | Middlesbrough FC | 2:1 |