1. Round | 26/08/2018 | Olympiakos Piraeus | - | Levadiakos | 1:0 | ||||
2. Round | 02/09/2018 | Olympiakos Piraeus | - | PAS Giannina | 5:0 | ||||
3. Round | 16/09/2018 | Olympiakos Piraeus | - | Asteras Tripolis | 2:1 | ||||
4. Round | 24/09/2018 | Panionios GSS | - | Olympiakos Piraeus | 0:1 | ||||
5. Round | 30/09/2018 | Olympiakos Piraeus | - | PAOK Saloniki | 0:1 | ||||
6. Round | 07/10/2018 | AEK Athen | - | Olympiakos Piraeus | 1:1 | ||||
7. Round | 21/10/2018 | OFI Heraklion | - | Olympiakos Piraeus | 1:0 | ||||
14. Round | 16/12/2018 | Olympiakos Piraeus | - | Lamia | 3:0 | ||||
15. Round | 30/01/2019 | Olympiakos Piraeus | - | AE Lárissa | 4:0 | ||||
21. Round | 17/02/2019 | Olympiakos Piraeus | - | AEK Athen | 4:1 | ||||
22. Round | 25/02/2019 | Olympiakos Piraeus | - | OFI Heraklion | 5:1 | ||||
27. Round | 07/04/2019 | Panetolikos | - | Olympiakos Piraeus | 0:5 | ||||
28. Round | 14/04/2019 | Olympiakos Piraeus | - | Xanthi FC | 4:0 | ||||
29. Round | 21/04/2019 | Lamia | - | Olympiakos Piraeus | 1:3 | ||||
30. Round | 05/05/2019 | AE Lárissa | - | Olympiakos Piraeus | 0:3 |