1st(1st leg) APOEL Nikosia - Doxa Katokopias 2:1 (0:1)
2nd (2nd leg) Doxa Katokopias - APOEL Nikosia 0:3 (0:2)
1st(1st leg): 02/01/2019 15:00 2nd (2nd leg): 20/02/2019 16:00 Winner: APOEL Nikosia
1st(1st leg) Ermis Aradippou - ASIL Lysi 3:0 (2:0)
2nd (2nd leg) ASIL Lysi - Ermis Aradippou 0:4 (0:2)
1st(1st leg): 02/01/2019 16:00 2nd (2nd leg): 16/01/2019 15:00 Winner: Ermis Aradippou
1st(1st leg) Apollon Limassol - Omonia Nikosia 1:0 (1:0)
2nd (2nd leg) Omonia Nikosia - Apollon Limassol 1:1 (0:0)
1st(1st leg): 02/01/2019 16:00 2nd (2nd leg): 16/01/2019 15:00 Winner: Apollon Limassol
1st(1st leg) Anorthosis Famagusta - Enosis Neon Paralimni 2:3 (2:1)
2nd (2nd leg) Enosis Neon Paralimni - Anorthosis Famagusta 0:0 (0:0)
1st(1st leg): 16/01/2019 14:00 2nd (2nd leg): 23/01/2019 16:00 Winner: Enosis Neon Paralimni
1st(1st leg) Aris Limassol - Paphos FC 2:1 (0:0)
2nd (2nd leg) Paphos FC - Aris Limassol 4:1 (1:1)
1st(1st leg): 16/01/2019 15:00 2nd (2nd leg): 23/01/2019 15:00 Winner: Paphos FC
1st(1st leg) Nea Salamina - AEK Larnaca 1:2 (1:1)
2nd (2nd leg) AEK Larnaca - Nea Salamina 2:0 (1:0)
1st(1st leg): 16/01/2019 16:30 2nd (2nd leg): 30/01/2019 16:00 Winner: AEK Larnaca
1st(1st leg) Karmiotissa Polemidion - Ethnikos Achna 2:1 (2:0)
2nd (2nd leg) Ethnikos Achna - Karmiotissa Polemidion 1:3 (0:0)
1st(1st leg): 23/01/2019 12:30 2nd (2nd leg): 20/02/2019 13:00 Winner: Karmiotissa Polemidion
1st(1st leg) AEL Limassol - ENTHOI Lakatamia 8:0 (6:0)
2nd (2nd leg) ENTHOI Lakatamia - AEL Limassol 0:6 (0:2)
1st(1st leg): 30/01/2019 15:00 2nd (2nd leg): 13/02/2019 15:00 Winner: AEL Limassol