1. Round | 17/08/2008 | Chelsea FC | - | Portsmouth FC | 4:0 | ![]() |
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2. Round | 24/08/2008 | Wigan Athletic | - | Chelsea FC | 0:1 | ||||
3. Round | 31/08/2008 | Chelsea FC | - | Tottenham Hotspur | 1:1 | ![]() |
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4. Round | 13/09/2008 | Manchester City | - | Chelsea FC | 1:3 | ||||
5. Round | 21/09/2008 | Chelsea FC | - | Manchester United | 1:1 | ||||
7. Round | 05/10/2008 | Chelsea FC | - | Aston Villa | 2:0 | ![]() |
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10. Round | 29/10/2008 | Hull City | - | Chelsea FC | 0:3 | ![]() |
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11. Round | 01/11/2008 | Chelsea FC | - | Sunderland AFC | 5:0 | ||||
14. Round | 22/11/2008 | Chelsea FC | - | Newcastle United | 0:0 | ||||
17. Round | 14/12/2008 | Chelsea FC | - | West Ham United | 1:1 | ||||
18. Round | 22/12/2008 | Everton FC | - | Chelsea FC | 0:0 | ||||
19. Round | 26/12/2008 | Chelsea FC | - | West Bromwich Albion | 2:0 | ||||
20. Round | 28/12/2008 | Fulham FC | - | Chelsea FC | 2:2 | ||||
21. Round | 11/01/2009 | Manchester United | - | Chelsea FC | 3:0 |