1. Round | 17/08/2008 | Chelsea FC | - | Portsmouth FC | 4:0 | ||||
6. Round | 27/09/2008 | Stoke City | - | Chelsea FC | 0:2 | ||||
8. Round | 18/10/2008 | Middlesbrough FC | - | Chelsea FC | 0:5 | ||||
12. Round | 09/11/2008 | Blackburn Rovers | - | Chelsea FC | 0:2 | ||||
13. Round | 15/11/2008 | West Bromwich Albion | - | Chelsea FC | 0:3 | ||||
16. Round | 06/12/2008 | Bolton Wanderers | - | Chelsea FC | 0:2 | ||||
26. Round | 21/02/2009 | Aston Villa | - | Chelsea FC | 0:1 |