| 1. Round | 20/08/2023 | Olympiakos Piraeus | - | Panserraikos | 2:0 |  |
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| 2. Round | 27/08/2023 | Olympiakos Piraeus | - | Atromitos | 4:0 | ||||
| 4. Round | 17/09/2023 | AEK Athen | - | Olympiakos Piraeus | 1:1 | ||||
| 5. Round | 24/09/2023 | Olympiakos Piraeus | - | AE Kifisias | 4:0 | ||||
| 9. Round | 30/10/2023 | OFI Heraklion | - | Olympiakos Piraeus | 0:2 | ||||
| 10. Round | 05/11/2023 | Olympiakos Piraeus | - | PAOK Saloniki | 2:4 | ||||
| 11. Round | 12/11/2023 | Asteras Tripolis | - | Olympiakos Piraeus | 0:2 |
Brazil
Italy 