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| 1st(1st leg) | AEK Larnaca | - | Karmiotissa Polemidion | 3:0 (0:0) | ||
| 2nd (2nd leg) | Karmiotissa Polemidion | - | AEK Larnaca | 0:1 (0:0) | ||
| 1st(1st leg): 08/01/2020 14:30 | 2nd (2nd leg): 22/01/2020 16:00 | Winner: AEK Larnaca | ||||
| 1st(1st leg) | Enosis Neon Paralimni | - | Doxa Katokopias | 0:2 (0:1) | ||
| 2nd (2nd leg) | Doxa Katokopias | - | Enosis Neon Paralimni | 1:1 (0:0) | ||
| 1st(1st leg): 08/01/2020 15:00 | 2nd (2nd leg): 22/01/2020 15:00 | Winner: Doxa Katokopias | ||||
| 1st(1st leg) | Alki Oroklini | - | AEL Limassol | 1:5 (1:2) | ||
| 2nd (2nd leg) | AEL Limassol | - | Alki Oroklini | 2:1 (0:1) | ||
| 1st(1st leg): 08/01/2020 17:00 | 2nd (2nd leg): 15/01/2020 14:00 | Winner: AEL Limassol | ||||
| 1st(1st leg) | Paphos FC | - | Nea Salamina | 0:1 (0:1) | ||
| 2nd (2nd leg) | Nea Salamina | - | Paphos FC | 2:1 (1:1) | ||
| 1st(1st leg): 15/01/2020 14:00 | 2nd (2nd leg): 29/01/2020 14:30 | Winner: Nea Salamina | ||||
| 1st(1st leg) | Olympiakos Nikosia | - | Anorthosis Famagusta | 0:0 (0:0) | ||
| 2nd (2nd leg) | Anorthosis Famagusta | - | Olympiakos Nikosia | 3:0 (2:0) | ||
| 1st(1st leg): 15/01/2020 15:00 | 2nd (2nd leg): 29/01/2020 17:00 | Winner: Anorthosis Famagusta | ||||
| 1st(1st leg) | Ermis Aradippou | - | Omonia Nikosia | 0:5 (0:3) | ||
| 2nd (2nd leg) | Omonia Nikosia | - | Ermis Aradippou | 3:0 (2:0) | ||
| 1st(1st leg): 15/01/2020 17:00 | 2nd (2nd leg): 22/01/2020 14:00 | Winner: Omonia Nikosia | ||||
| 1st(1st leg) | Apollon Limassol | - | APOEL Nikosia | 1:0 (1:0) | ||
| 2nd (2nd leg) | APOEL Nikosia | - | Apollon Limassol | 1:2 (0:1) | ||
| 1st(1st leg): 22/01/2020 17:00 | 2nd (2nd leg): 29/01/2020 14:30 | Winner: Apollon Limassol | ||||
| 1st(1st leg) | Dighenis Morphou | - | Ethnikos Achna | 0:3 (0:1) | ||
| 2nd (2nd leg) | Ethnikos Achna | - | Dighenis Morphou | 3:0 (1:0) | ||
| 1st(1st leg): 29/01/2020 12:30 | 2nd (2nd leg): 05/02/2020 12:30 | Winner: Ethnikos Achna | ||||
