Chania-Kissamikos 1-6 AEK Athens *
| 23.01.2019 | AEK Athens | 5-0 | Chania-Kissamikos | |
| 09.01.2019 | Chania-Kissamikos | 1-1 | AEK Athens | |
Apollon Smyrni 1-5 Atromitos FC *
| 23.01.2019 | Atromitos FC | 2-1 | Apollon Smyrni | |
| 09.01.2019 | Apollon Smyrni | 0-3 | Atromitos FC | |
AE Larisa 6-7 Asteras Tripoli *
| 23.01.2019 | Asteras Tripoli | 5-3 | AE Larisa | |
| 09.01.2019 | AE Larisa | 3-2 | Asteras Tripoli | |
*Lamia FC 1-1 Panathinaikos
| 24.01.2019 | Panathinaikos | 1-0/p.2-4 | Lamia FC | |
| 10.01.2019 | Lamia FC | 1-0 | Panathinaikos | |
*Ergotelis Creta 2-2 OFI Creta
| 24.01.2019 | OFI Creta | 1-1/p.3-4 | Ergotelis Creta | |
| 08.01.2019 | Ergotelis Creta | 1-1 | OFI Creta | |
SKODA Xanthi 1-3 Olympiakos Pireus *
| 23.01.2019 | Olympiakos Pireus | 3-1 | SKODA Xanthi | |
| 08.01.2019 | SKODA Xanthi | 0-0 | Olympiakos Pireus | |
Panachaiki FC 2-6 PAOK Salonica *
| 22.01.2019 | PAOK Salonica | 5-0 | Panachaiki FC | |
| 08.01.2019 | Panachaiki FC | 2-1 | PAOK Salonica | |
PAS Giannina 1-3 Panionios GSS *
| 22.01.2019 | Panionios GSS | 2-0 | PAS Giannina | |
| 08.01.2019 | PAS Giannina | 1-1 | Panionios GSS | |