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 | ||||
4. Ronde | 13.09.2008 | Portsmouth FC | - | Middlesbrough FC | 2:1 | ||||
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 | ||||
11. Ronde | 01.11.2008 | Middlesbrough FC | - | West Ham United | 1:1 | ||||
15. Ronde | 29.11.2008 | Middlesbrough FC | - | Newcastle United | 0:0 | ||||
18. Ronde | 20.12.2008 | Fulham FC | - | Middlesbrough FC | 3:0 | ||||
19. Ronde | 26.12.2008 | Middlesbrough FC | - | Everton FC | 0:1 | ||||
21. Ronde | 10.01.2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
22. Ronde | 17.01.2009 | West Bromwich Albion | - | Middlesbrough FC | 3:0 |