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| H (Match allé) | AEK Larnaca | - | Karmiotissa Polemidion | 3:0 (0:0) | ||
| R (match retour) | Karmiotissa Polemidion | - | AEK Larnaca | 0:1 (0:0) | ||
| H (Match allé): 08.01.2020 15:30 | R (match retour): 22.01.2020 17:00 | vainqueur: AEK Larnaca | ||||
| H (Match allé) | Enosis Neon Paralimni | - | Doxa Katokopias | 0:2 (0:1) | ||
| R (match retour) | Doxa Katokopias | - | Enosis Neon Paralimni | 1:1 (0:0) | ||
| H (Match allé): 08.01.2020 16:00 | R (match retour): 22.01.2020 16:00 | vainqueur: Doxa Katokopias | ||||
| H (Match allé) | Alki Oroklini | - | AEL Limassol | 1:5 (1:2) | ||
| R (match retour) | AEL Limassol | - | Alki Oroklini | 2:1 (0:1) | ||
| H (Match allé): 08.01.2020 18:00 | R (match retour): 15.01.2020 15:00 | vainqueur: AEL Limassol | ||||
| H (Match allé) | Paphos FC | - | Nea Salamina | 0:1 (0:1) | ||
| R (match retour) | Nea Salamina | - | Paphos FC | 2:1 (1:1) | ||
| H (Match allé): 15.01.2020 15:00 | R (match retour): 29.01.2020 15:30 | vainqueur: Nea Salamina | ||||
| H (Match allé) | Olympiakos Nikosia | - | Anorthosis Famagusta | 0:0 (0:0) | ||
| R (match retour) | Anorthosis Famagusta | - | Olympiakos Nikosia | 3:0 (2:0) | ||
| H (Match allé): 15.01.2020 16:00 | R (match retour): 29.01.2020 18:00 | vainqueur: Anorthosis Famagusta | ||||
| H (Match allé) | Ermis Aradippou | - | Omonia Nikosia | 0:5 (0:3) | ||
| R (match retour) | Omonia Nikosia | - | Ermis Aradippou | 3:0 (2:0) | ||
| H (Match allé): 15.01.2020 18:00 | R (match retour): 22.01.2020 15:00 | vainqueur: Omonia Nikosia | ||||
| H (Match allé) | Apollon Limassol | - | APOEL Nikosia | 1:0 (1:0) | ||
| R (match retour) | APOEL Nikosia | - | Apollon Limassol | 1:2 (0:1) | ||
| H (Match allé): 22.01.2020 18:00 | R (match retour): 29.01.2020 15:30 | vainqueur: Apollon Limassol | ||||
| H (Match allé) | Dighenis Morphou | - | Ethnikos Achna | 0:3 (0:1) | ||
| R (match retour) | Ethnikos Achna | - | Dighenis Morphou | 3:0 (1:0) | ||
| H (Match allé): 29.01.2020 13:30 | R (match retour): 05.02.2020 13:30 | vainqueur: Ethnikos Achna | ||||
