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 |