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| 13/09/2023 | Panthrakikos | - | Ethnikos Piraeus | 0:3 dec. | ||
| OFI Ierapetra | - | Kampaniakos FC | 0:3 dec. | |||
| 12:00 | Asteras Stavros | - | AO Giouchtas | 1:3 (1:1) | ||
| 14:00 | Acharnaikos FC | - | Panachaiki GE | 3:2 (0:0, 0:0, 0:0) pso | ||
| 14:00 | AO Chanioti | - | AO Tilikratis | 0:1 (0:0) | ||
| 14:00 | Panargiakos FC | - | PAO Vardas | 3:4 (0:1) pso | ||
| 14:00 | Ionikos Nikea | - | GS Kallithea | 0:3 (0:2) | ||
| 14:00 | Apollon Paralimniou | - | Alexandroupoli FC | 3:0 (2:0) | ||
| 14:00 | Makedonikos FC | - | AO Egaleo | 0:4 (0:1) | ||
| 14:00 | GS Ilioupolis | - | Levadiakos | 1:2 (0:0) | ||
| 17/09/2023 | 14:00 | PAE Chania | - | Apollon Pontou | 2:1 (1:1) | |
| 14:00 | Kozani FC | - | AEP Iraklis FC | 2:1 (1:1) | ||
| 20/09/2023 | 14:00 | APS Zakynthos | - | Niki Volou FC | 0:1 (0:0) | |
| 27/09/2023 | 13:00 | Aiolikos Mytilinis | - | Anagennisi Karditsa | 3:0 dec. |
