1. Round | 24/08/2019 | Olympiakos Piraeus | - | Asteras Tripolis | 1:0 | ||||
2. Round | 01/09/2019 | AE Lárissa | - | Olympiakos Piraeus | 0:1 | ||||
3. Round | 14/09/2019 | Olympiakos Piraeus | - | Volos NFC | 5:0 | ||||
5. Round | 28/09/2019 | Olympiakos Piraeus | - | Lamia | 2:0 | ||||
7. Round | 19/10/2019 | Olympiakos Piraeus | - | OFI Heraklion | 2:1 | ||||
17. Round | 05/01/2020 | Olympiakos Piraeus | - | Panathinaikos | 1:0 |