| 1. Jornada | 17.08.2008 | Chelsea | - | Portsmouth FC | 4:0 | ||||
| 2. Jornada | 24.08.2008 | Wigan Athletic | - | Chelsea | 0:1 |  |
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| 3. Jornada | 31.08.2008 | Chelsea | - | Tottenham Hotspur | 1:1 | ||||
| 4. Jornada | 13.09.2008 | Manchester City | - | Chelsea | 1:3 |  |
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| 5. Jornada | 21.09.2008 | Chelsea | - | Manchester United | 1:1 | ||||
| 9. Jornada | 26.10.2008 | Chelsea | - | Liverpool | 0:1 | ||||
| 10. Jornada | 29.10.2008 | Hull City | - | Chelsea | 0:3 | ||||
| 20. Jornada | 28.12.2008 | Fulham FC | - | Chelsea | 2:2 | ||||
| 21. Jornada | 11.01.2009 | Manchester United | - | Chelsea | 3:0 | |
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| 22. Jornada | 17.01.2009 | Chelsea | - | Stoke City | 2:1 | ||||
| 29. Jornada | 15.03.2009 | Chelsea | - | Manchester City | 1:0 | ||||
| 32. Jornada | 11.04.2009 | Chelsea | - | Bolton Wanderers | 4:3 |
Portugal
