| 3. Round | 14/01/2009 | Southend United | - | Chelsea FC | 1:4 |  |
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| 4. Round | 24/01/2009 | Chelsea FC | - | Ipswich Town | 3:1 | |
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| Round of 16 | 14/02/2009 | Watford FC | - | Chelsea FC | 1:3 | ||||
| Quarter-finals | 07/03/2009 | Coventry City | - | Chelsea FC | 0:2 | ||||
| Semi-finals | 18/04/2009 | Arsenal FC | - | Chelsea FC | 1:2 |  |
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| Final | 30/05/2009 | Chelsea FC | - | Everton FC | 2:1 |
Germany
