| 1. Round | 18/09/2008 | Beşiktaş | - | Metalist Kharkiv | 1:0 | ||||
| 1. Round | 02/10/2008 | Metalist Kharkiv | - | Beşiktaş | 4:1 | ||||
| Group B | 06/11/2008 | Metalist Kharkiv | - | Hertha BSC | 0:0 | ||||
| Group B | 27/11/2008 | Galatasaray | - | Metalist Kharkiv | 0:1 | ||||
| Group B | 03/12/2008 | Metalist Kharkiv | - | Olympiakos Piraeus | 1:0 | ||||
| Group B | 18/12/2008 | SL Benfica | - | Metalist Kharkiv | 0:1 |  |
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| 3. Round | 18/02/2009 | Sampdoria | - | Metalist Kharkiv | 0:1 | ||||
| 3. Round | 26/02/2009 | Metalist Kharkiv | - | Sampdoria | 2:0 | ||||
| Round of 16 | 12/03/2009 | Dinamo Kiev | - | Metalist Kharkiv | 1:0 | ||||
| Round of 16 | 19/03/2009 | Metalist Kharkiv | - | Dinamo Kiev | 3:2 |
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