| 1. Round | 18/09/2008 | Cherno More Varna | - | VfB Stuttgart | 1:2 | ||||
| 1. Round | 02/10/2008 | VfB Stuttgart | - | Cherno More Varna | 2:2 |  |
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| Group C | 23/10/2008 | Sevilla FC | - | VfB Stuttgart | 2:0 | ||||
| Group C | 06/11/2008 | VfB Stuttgart | - | Partizan | 2:0 | ||||
| Group C | 27/11/2008 | Sampdoria | - | VfB Stuttgart | 1:1 | ||||
| Group C | 18/12/2008 | VfB Stuttgart | - | Standard Liège | 3:0 | ||||
| 3. Round | 18/02/2009 | Zenit St. Petersburg | - | VfB Stuttgart | 2:1 | ||||
| 3. Round | 26/02/2009 | VfB Stuttgart | - | Zenit St. Petersburg | 1:2 |
Germany