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| 1st(1st leg) | Apollon Lárissa | - | Xanthi FC | 2:1 (0:1) | ||
| 2nd (2nd leg) | Xanthi FC | - | Apollon Lárissa | 3:0 (2:0) | ||
| 1st(1st leg): 29/10/2019 13:00 | 2nd (2nd leg): 04/12/2019 15:15 | Winner: Xanthi FC | ||||
| 1st(1st leg) | Panserraikos | - | Volos NFC | 1:1 (0:0) | ||
| 2nd (2nd leg) | Volos NFC | - | Panserraikos | 4:2 (1:0, 1:1, 1:1) pso | ||
| 1st(1st leg): 29/10/2019 15:15 | 2nd (2nd leg): 05/12/2019 15:15 | Winner: Volos NFC | ||||
| 1st(1st leg) | PAS Giannina | - | Veria FC | 1:0 (0:0) | ||
| 2nd (2nd leg) | Veria FC | - | PAS Giannina | 1:2 (1:1) | ||
| 1st(1st leg): 29/10/2019 17:30 | 2nd (2nd leg): 04/12/2019 17:30 | Winner: PAS Giannina | ||||
| 1st(1st leg) | Olympiakos Volou | - | Panionios GSS | 0:3 (0:0) | ||
| 2nd (2nd leg) | Panionios GSS | - | Olympiakos Volou | 6:0 (3:0) | ||
| 1st(1st leg): 30/10/2019 13:00 | 2nd (2nd leg): 04/12/2019 15:15 | Winner: Panionios GSS | ||||
| 1st(1st leg) | Kalamata | - | AE Lárissa | 3:0 (1:0) | ||
| 2nd (2nd leg) | AE Lárissa | - | Kalamata | 1:0 (0:0) | ||
| 1st(1st leg): 30/10/2019 13:00 | 2nd (2nd leg): 04/12/2019 17:30 | Winner: Kalamata | ||||
| 1st(1st leg) | AO Kavala | - | OFI Heraklion | 2:0 (2:0) | ||
| 2nd (2nd leg) | OFI Heraklion | - | AO Kavala | 4:0 (1:0) | ||
| 1st(1st leg): 30/10/2019 15:15 | 2nd (2nd leg): 04/12/2019 13:00 | Winner: OFI Heraklion | ||||
| 1st(1st leg) | Panachaiki GE | - | Panathinaikos | 1:3 (0:2) | ||
| 2nd (2nd leg) | Panathinaikos | - | Panachaiki GE | 2:0 (0:0) | ||
| 1st(1st leg): 30/10/2019 17:30 | 2nd (2nd leg): 05/12/2019 17:30 | Winner: Panathinaikos | ||||
| 1st(1st leg) | Platanias Chanion | - | Asteras Tripolis | 0:1 (0:0) | ||
| 2nd (2nd leg) | Asteras Tripolis | - | Platanias Chanion | 3:2 (0:1, 0:1) aet | ||
| 1st(1st leg): 31/10/2019 13:00 | 2nd (2nd leg): 04/12/2019 13:00 | Winner: Asteras Tripolis | ||||
| 1st(1st leg) | PAE Ialysos | - | Panetolikos | 0:4 (0:1) | ||
| 2nd (2nd leg) | Panetolikos | - | PAE Ialysos | 5:1 (0:0) | ||
| 1st(1st leg): 31/10/2019 13:00 | 2nd (2nd leg): 03/12/2019 11:45 | Winner: Panetolikos | ||||
| 1st(1st leg) | Aiolikos Mytilinis | - | Lamia | 0:3 (0:2) | ||
| 2nd (2nd leg) | Lamia | - | Aiolikos Mytilinis | 3:0 (2:0) | ||
| 1st(1st leg): 31/10/2019 15:15 | 2nd (2nd leg): 05/12/2019 13:00 | Winner: Lamia | ||||
| 1st(1st leg) | AO Trikala | - | Ergotelis | 3:2 (0:0) | ||
| 2nd (2nd leg) | Ergotelis | - | AO Trikala | 0:1 (0:1) | ||
| 1st(1st leg): 31/10/2019 17:30 | 2nd (2nd leg): 03/12/2019 15:15 | Winner: AO Trikala | ||||
