AO Trikala 1-2 Lamia FC *
| 15.01.2020 | Lamia FC | 1-1 | AO Trikala | |
| 09.01.2020 | AO Trikala | 0-1 | Lamia FC | |
AO Xanthi 1-3 Aris Salonica *
| 14.01.2020 | Aris Salonica | 2-1 | AO Xanthi | |
| 08.01.2020 | AO Xanthi | 0-1 | Aris Salonica | |
Asteras Tripoli 1-3 AEK Athens *
| 30.01.2020 | AEK Athens | 2-0 | Asteras Tripoli | |
| 16.01.2020 | Asteras Tripoli | 1-1 | AEK Athens | |
Kalamata 1-6 Olympiakos Pireus *
| 15.01.2020 | Olympiakos Pireus | 4-1 | Kalamata | |
| 08.01.2020 | Kalamata | 0-2 | Olympiakos Pireus | |
PAS Giannina 2-3 Panathinaikos *
| 15.01.2020 | Panathinaikos | 3-1 | PAS Giannina | |
| 08.01.2020 | PAS Giannina | 1-0 | Panathinaikos | |
*Panetolikos 1-1 Panionios GSS
| 15.01.2020 | Panionios GSS | 1-1 AET | Panetolikos | |
| 08.01.2020 | Panetolikos | 0-0 | Panionios GSS | |
OFI Creta 1-7 PAOK Salonica *
| 15.01.2020 | PAOK Salonica | 4-1 | OFI Creta | |
| 07.01.2020 | OFI Creta | 0-3 | PAOK Salonica | |
Volos NFC 2-3 Atromitos FC *
| 14.01.2020 | Atromitos FC | 0-2 | Volos NFC | |
| 07.01.2020 | Volos NFC | 0-3 | Atromitos FC | |