| 9. Jornada | 10.11.2019 | Olympiacos Nikosia | - | Ethnikos Achna | 4:0 | ||||
| 11. Jornada | 29.11.2019 | Olympiacos Nikosia | - | Enosis Neon Paralimni | 0:0 | ||||
| 12. Jornada | 07.12.2019 | Olympiacos Nikosia | - | APOEL Nikosia | 2:0 | ||||
| 13. Jornada | 13.12.2019 | Doxa Katokopias | - | Olympiacos Nikosia | 2:6 | ||||
| 14. Jornada | 22.12.2019 | Olympiacos Nikosia | - | Nea Salamina | 0:3 | ||||
| 1. Jornada | 08.01.2020 | APOEL Nikosia | - | Olympiacos Nikosia | 4:2 | ||||
| 16. Jornada | 12.01.2020 | Olympiacos Nikosia | - | Apollon Limassol | 0:2 | ||||
| 17. Jornada | 25.01.2020 | Paphos FC | - | Olympiacos Nikosia | 1:1 |
Portugal