1. Round | 16/08/2008 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
24. Round | 31/01/2009 | Middlesbrough FC | - | Blackburn Rovers | 0:0 | ||||
25. Round | 07/02/2009 | Manchester City | - | Middlesbrough FC | 1:0 | ||||
26. Round | 21/02/2009 | Middlesbrough FC | - | Wigan Athletic | 0:0 | ||||
27. Round | 28/02/2009 | Middlesbrough FC | - | Liverpool FC | 2:0 | ||||
28. Round | 04/03/2009 | Tottenham Hotspur | - | Middlesbrough FC | 4:0 | ||||
29. Round | 14/03/2009 | Middlesbrough FC | - | Portsmouth FC | 1:1 | ||||
30. Round | 21/03/2009 | Stoke City | - | Middlesbrough FC | 1:0 | ||||
31. Round | 04/04/2009 | Bolton Wanderers | - | Middlesbrough FC | 4:1 | ||||
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 | ||||
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 |