1. Round | 17/08/2008 | Chelsea FC | - | Portsmouth FC | 4:0 | ||||
2. Round | 24/08/2008 | Wigan Athletic | - | Chelsea FC | 0:1 | ||||
3. Round | 31/08/2008 | Chelsea FC | - | Tottenham Hotspur | 1:1 | ||||
4. Round | 13/09/2008 | Manchester City | - | Chelsea FC | 1:3 | ||||
5. Round | 21/09/2008 | Chelsea FC | - | Manchester United | 1:1 | ||||
9. Round | 26/10/2008 | Chelsea FC | - | Liverpool FC | 0:1 | ||||
10. Round | 29/10/2008 | Hull City | - | Chelsea FC | 0:3 | ||||
20. Round | 28/12/2008 | Fulham FC | - | Chelsea FC | 2:2 | ||||
21. Round | 11/01/2009 | Manchester United | - | Chelsea FC | 3:0 | ||||
22. Round | 17/01/2009 | Chelsea FC | - | Stoke City | 2:1 | ||||
29. Round | 15/03/2009 | Chelsea FC | - | Manchester City | 1:0 | ||||
32. Round | 11/04/2009 | Chelsea FC | - | Bolton Wanderers | 4:3 |