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| 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 | ||||
