| 1. Round | 16/09/2008 | FC Nordsjælland | - | Olympiakos Piraeus | 0:2 | ||||
| 1. Round | 02/10/2008 | Olympiakos Piraeus | - | FC Nordsjælland | 5:0 | ||||
| Group B | 23/10/2008 | Galatasaray | - | Olympiakos Piraeus | 1:0 |  |
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| Group B | 27/11/2008 | Olympiakos Piraeus | - | SL Benfica | 5:1 | ||||
| Group B | 03/12/2008 | Metalist Kharkiv | - | Olympiakos Piraeus | 1:0 | |
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| Group B | 18/12/2008 | Olympiakos Piraeus | - | Hertha BSC | 4:0 | ||||
| 3. Round | 18/02/2009 | Olympiakos Piraeus | - | AS Saint-Étienne | 1:3 |
France