2. Round | 01/09/2019 | AE Lárissa | - | Olympiakos Piraeus | 0:1 | ||||
3. Round | 14/09/2019 | Olympiakos Piraeus | - | Volos NFC | 5:0 | ||||
4. Round | 22/09/2019 | Panathinaikos | - | Olympiakos Piraeus | 1:1 | ||||
10. Round | 10/11/2019 | Olympiakos Piraeus | - | Atromitos | 2:0 | ||||
11. Round | 23/11/2019 | Panionios GSS | - | Olympiakos Piraeus | 1:1 |