4. Round | 27/09/2008 | OFI Heraklion | - | Olympiakos Piraeus | 0:0 | ||||
6. Round | 19/10/2008 | Olympiakos Piraeus | - | Panthrakikos | 2:0 | ||||
8. Round | 02/11/2008 | Olympiakos Piraeus | - | Ergotelis | 2:0 | ||||
12. Round | 30/11/2008 | Olympiakos Piraeus | - | Panionios GSS | 4:1 | ||||
13. Round | 07/12/2008 | Olympiakos Piraeus | - | Levadiakos | 1:0 | ||||
15. Round | 21/12/2008 | Olympiakos Piraeus | - | Thrasyvoulos Fylis | 2:1 |