| 2. Round | 30/08/2014 | Panetolikos | - | Olympiakos Piraeus | 1:1 | ||||
| 3. Round | 13/09/2014 | Olympiakos Piraeus | - | OFI Heraklion | 3:0 | ||||
| 10. Round | 09/11/2014 | Olympiakos Piraeus | - | Panthrakikos | 5:1 | ||||
| 12. Round | 30/11/2014 | AO Kerkyra | - | Olympiakos Piraeus | 0:4 | ||||
| 13. Round | 06/12/2014 | Olympiakos Piraeus | - | PAS Giannina | 2:2 | ||||
| 16. Round | 20/12/2014 | AEL Kalloni | - | Olympiakos Piraeus | 0:5 |  |
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| 11. Round | 11/01/2015 | Skoda Xanthi | - | Olympiakos Piraeus | 1:3 | ||||
| 19. Round | 18/01/2015 | Olympiakos Piraeus | - | Panetolikos | 2:0 | ||||
| 27. Round | 15/04/2015 | Panthrakikos | - | Olympiakos Piraeus | 1:3 |  |
Greece