1. Round | 16/08/2008 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
2. Round | 23/08/2008 | Liverpool FC | - | Middlesbrough FC | 2:1 | ||||
3. Round | 30/08/2008 | Middlesbrough FC | - | Stoke City | 2:1 | ||||
5. Round | 20/09/2008 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
6. Round | 27/09/2008 | Middlesbrough FC | - | West Bromwich Albion | 0:1 | ||||
7. Round | 04/10/2008 | Wigan Athletic | - | Middlesbrough FC | 0:1 | ||||
8. Round | 18/10/2008 | Middlesbrough FC | - | Chelsea FC | 0:5 | ||||
17. Round | 13/12/2008 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
18. Round | 20/12/2008 | Fulham FC | - | Middlesbrough FC | 3:0 | ||||
22. Round | 17/01/2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
23. Round | 28/01/2009 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
30. Round | 21/03/2009 | Stoke City | - | Middlesbrough FC | 1:0 | ||||
36. Round | 11/05/2009 | Newcastle United | - | Middlesbrough FC | 3:1 |