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| U | Apollon Lárissa | - | Xanthi FC | 2:1 (0:1) | ||
| R | Xanthi FC | - | Apollon Lárissa | 3:0 (2:0) | ||
| U: 29.10.2019 14:00 | R: 04.12.2019 16:15 | Winnaars: Xanthi FC | ||||
| U | Panserraikos | - | Volos NFC | 1:1 (0:0) | ||
| R | Volos NFC | - | Panserraikos | 4:2 (1:0, 1:1, 1:1) d.p. | ||
| U: 29.10.2019 16:15 | R: 05.12.2019 16:15 | Winnaars: Volos NFC | ||||
| U | PAS Giannina | - | Veria FC | 1:0 (0:0) | ||
| R | Veria FC | - | PAS Giannina | 1:2 (1:1) | ||
| U: 29.10.2019 18:30 | R: 04.12.2019 18:30 | Winnaars: PAS Giannina | ||||
| U | Olympiakos Volou | - | Panionios GSS | 0:3 (0:0) | ||
| R | Panionios GSS | - | Olympiakos Volou | 6:0 (3:0) | ||
| U: 30.10.2019 14:00 | R: 04.12.2019 16:15 | Winnaars: Panionios GSS | ||||
| U | PS Kalamata | - | AE Lárissa | 3:0 (1:0) | ||
| R | AE Lárissa | - | PS Kalamata | 1:0 (0:0) | ||
| U: 30.10.2019 14:00 | R: 04.12.2019 18:30 | Winnaars: PS Kalamata | ||||
| U | AO Kavala | - | OFI Heraklion | 2:0 (2:0) | ||
| R | OFI Heraklion | - | AO Kavala | 4:0 (1:0) | ||
| U: 30.10.2019 16:15 | R: 04.12.2019 14:00 | Winnaars: OFI Heraklion | ||||
| U | Panachaiki GE | - | Panathinaikos | 1:3 (0:2) | ||
| R | Panathinaikos | - | Panachaiki GE | 2:0 (0:0) | ||
| U: 30.10.2019 18:30 | R: 05.12.2019 18:30 | Winnaars: Panathinaikos | ||||
| U | Platanias Chanion | - | Asteras Tripolis | 0:1 (0:0) | ||
| R | Asteras Tripolis | - | Platanias Chanion | 3:2 (0:1, 0:1) n.v. | ||
| U: 31.10.2019 14:00 | R: 04.12.2019 14:00 | Winnaars: Asteras Tripolis | ||||
| U | PAE Ialysos | - | Panetolikos | 0:4 (0:1) | ||
| R | Panetolikos | - | PAE Ialysos | 5:1 (0:0) | ||
| U: 31.10.2019 14:00 | R: 03.12.2019 12:45 | Winnaars: Panetolikos | ||||
| U | Aiolikos Mytilinis | - | Lamia | 0:3 (0:2) | ||
| R | Lamia | - | Aiolikos Mytilinis | 3:0 (2:0) | ||
| U: 31.10.2019 16:15 | R: 05.12.2019 14:00 | Winnaars: Lamia | ||||
| U | AO Trikala | - | Ergotelis | 3:2 (0:0) | ||
| R | Ergotelis | - | AO Trikala | 0:1 (0:1) | ||
| U: 31.10.2019 18:30 | R: 03.12.2019 16:15 | Winnaars: AO Trikala | ||||
