1st(1st leg) PAS Giannina - Panionios GSS 1:1 (1:1)
2nd (2nd leg) Panionios GSS - PAS Giannina 2:0 (0:0)
1st(1st leg): 08/01/2019 13:00 2nd (2nd leg): 22/01/2019 13:00 Winner: Panionios GSS
1st(1st leg) Panachaiki GE - PAOK Saloniki 2:1 (1:0)
2nd (2nd leg) PAOK Saloniki - Panachaiki GE 5:0 (2:0)
1st(1st leg): 08/01/2019 15:00 2nd (2nd leg): 22/01/2019 17:30 Winner: PAOK Saloniki
1st(1st leg) Xanthi FC - Olympiakos Piraeus 0:0 (0:0)
2nd (2nd leg) Olympiakos Piraeus - Xanthi FC 3:1 (1:0)
1st(1st leg): 08/01/2019 15:15 2nd (2nd leg): 23/01/2019 17:30 Winner: Olympiakos Piraeus
1st(1st leg) Ergotelis - OFI Heraklion 1:1 (0:1)
2nd (2nd leg) OFI Heraklion - Ergotelis 3:4 (1:1, 1:1, 1:1) pso
1st(1st leg): 08/01/2019 17:30 2nd (2nd leg): 24/01/2019 15:15 Winner: Ergotelis
1st(1st leg) Apollon Smyrnis - Atromitos 0:3 (0:1)
2nd (2nd leg) Atromitos - Apollon Smyrnis 2:1 (1:0)
1st(1st leg): 09/01/2019 13:00 2nd (2nd leg): 23/01/2019 13:00 Winner: Atromitos
1st(1st leg) AE Lárissa - Asteras Tripolis 3:2 (3:1)
2nd (2nd leg) Asteras Tripolis - AE Lárissa 5:3 (2:0)
1st(1st leg): 09/01/2019 15:15 2nd (2nd leg): 23/01/2019 15:15 Winner: Asteras Tripolis
1st(1st leg) Chania Kissamikos - AEK Athen 1:1 (0:1)
2nd (2nd leg) AEK Athen - Chania Kissamikos 5:0 (2:0)
1st(1st leg): 09/01/2019 17:30 2nd (2nd leg): 23/01/2019 15:15 Winner: AEK Athen
1st(1st leg) Lamia - Panathinaikos 1:0 (0:0)
2nd (2nd leg) Panathinaikos - Lamia 2:4 (0:0, 1:0, 1:0) pso
1st(1st leg): 10/01/2019 17:30 2nd (2nd leg): 24/01/2019 17:30 Winner: Lamia