1. Ronde | 16.08.2008 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
2. Ronde | 23.08.2008 | Liverpool FC | - | Middlesbrough FC | 2:1 | ||||
3. Ronde | 30.08.2008 | Middlesbrough FC | - | Stoke City | 2:1 | ||||
5. Ronde | 20.09.2008 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
6. Ronde | 27.09.2008 | Middlesbrough FC | - | West Bromwich Albion | 0:1 | ||||
7. Ronde | 04.10.2008 | Wigan Athletic | - | Middlesbrough FC | 0:1 | ||||
8. Ronde | 18.10.2008 | Middlesbrough FC | - | Chelsea FC | 0:5 | ||||
17. Ronde | 13.12.2008 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
18. Ronde | 20.12.2008 | Fulham FC | - | Middlesbrough FC | 3:0 | ||||
22. Ronde | 17.01.2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
23. Ronde | 28.01.2009 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
30. Ronde | 21.03.2009 | Stoke City | - | Middlesbrough FC | 1:0 | ||||
36. Ronde | 11.05.2009 | Newcastle United | - | Middlesbrough FC | 3:1 |