| Group A | 16/09/2008 | Chelsea FC | - | Girondins Bordeaux | 4:0 | ||||
| Group A | 01/10/2008 | CFR Cluj | - | Chelsea FC | 0:0 | ||||
| Group A | 22/10/2008 | Chelsea FC | - | AS Roma | 1:0 |  |
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| Group A | 04/11/2008 | AS Roma | - | Chelsea FC | 3:1 | |
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| Group A | 26/11/2008 | Girondins Bordeaux | - | Chelsea FC | 1:1 | |
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| Group A | 09/12/2008 | Chelsea FC | - | CFR Cluj | 2:1 | ||||
| Round of 16 | 25/02/2009 | Chelsea FC | - | Juventus | 1:0 | ||||
| Round of 16 | 10/03/2009 | Juventus | - | Chelsea FC | 2:2 | ||||
| Quarter-finals | 08/04/2009 | Liverpool FC | - | Chelsea FC | 1:3 | |
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| Semi-finals | 28/04/2009 | FC Barcelona | - | Chelsea FC | 0:0 | ||||
| Semi-finals | 06/05/2009 | Chelsea FC | - | FC Barcelona | 1:1 |
England
