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 | ||||
21. Round | 26/01/2020 | AEK Athen | - | Olympiakos Piraeus | 0:0 | ||||
24. Round | 15/02/2020 | Olympiakos Piraeus | - | Panionios GSS | 4:0 | ||||
26. Round | 01/03/2020 | Olympiakos Piraeus | - | Panetolikos | 2:0 |