| 1. Jornada | 16.08.2008 | Middlesbrough | - | Tottenham Hotspur | 2:1 |  |
|||
| 2. Jornada | 23.08.2008 | Liverpool | - | Middlesbrough | 2:1 | |
 |
||
| 3. Jornada | 30.08.2008 | Middlesbrough | - | Stoke City | 2:1 | ||||
| 4. Jornada | 13.09.2008 | Portsmouth FC | - | Middlesbrough | 2:1 | |
|
||
| 6. Jornada | 27.09.2008 | Middlesbrough | - | West Bromwich Albion | 0:1 | |
|||
| 7. Jornada | 04.10.2008 | Wigan Athletic | - | Middlesbrough | 0:1 | ||||
| 8. Jornada | 18.10.2008 | Middlesbrough | - | Chelsea | 0:5 | ||||
| 11. Jornada | 01.11.2008 | Middlesbrough | - | West Ham United | 1:1 | |
|||
| 15. Jornada | 29.11.2008 | Middlesbrough | - | Newcastle United | 0:0 | ||||
| 18. Jornada | 20.12.2008 | Fulham FC | - | Middlesbrough | 3:0 | ||||
| 19. Jornada | 26.12.2008 | Middlesbrough | - | Everton | 0:1 | ||||
| 21. Jornada | 10.01.2009 | Middlesbrough | - | Sunderland | 1:1 | ||||
| 22. Jornada | 17.01.2009 | West Bromwich Albion | - | Middlesbrough | 3:0 |
Egipto