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| 24/09/2019 | 14:00 | AO Trikala | - | Doxa Dramas FC | 1:0 | |
| 14:00 | Ionikos Nikea | - | Panachaiki GE | 1:2 | ||
| 14:00 | Veria FC | - | Levadiakos | 3:0 | ||
| 25/09/2019 | 14:00 | Kalamata | - | AE Karaiskakis | 4:3 pso | |
| 14:00 | AO Egaleo | - | Ergotelis | 0:2 | ||
| 14:00 | AO Kavala | - | PAE Chania | 2:0 | ||
| 26/09/2019 | 09:00 | Panthiraikos | - | Platanias Chanion | 1:2 | |
| 02/10/2019 | 12:30 | PAE Ialysos | - | AO Kerkyra | 1:0 | |
| 14:00 | Aspropyrgos | - | PAS Giannina | 0:2 | ||
| 14:00 | Aetos Orfano | - | Apollon Lárissa | 0:1 | ||
| 09/10/2019 | 14:00 | Olympiakos Volou | - | Apollon Pontou | 1:0 | |
| 23/10/2019 | 14:00 | Aiolikos Mytilinis | - | Apollon Smyrnis | 1:0 |
