| 2. Round | 01/09/2019 | Olympiakos Nikosia | - | Doxa Katokopias | 1:1 | ||||
| 3. Round | 16/09/2019 | Nea Salamina | - | Olympiakos Nikosia | 3:2 | ||||
| 5. Round | 06/10/2019 | Apollon Limassol | - | Olympiakos Nikosia | 3:1 | ||||
| 9. Round | 10/11/2019 | Olympiakos Nikosia | - | Ethnikos Achna | 4:0 | ||||
| 10. Round | 24/11/2019 | AEL Limassol | - | Olympiakos Nikosia | 0:0 | ||||
| 11. Round | 29/11/2019 | Olympiakos Nikosia | - | Enosis Neon Paralimni | 0:0 | ||||
| 12. Round | 07/12/2019 | Olympiakos Nikosia | - | APOEL Nikosia | 2:0 | ||||
| 13. Round | 13/12/2019 | Doxa Katokopias | - | Olympiakos Nikosia | 2:6 | ||||
| 14. Round | 22/12/2019 | Olympiakos Nikosia | - | Nea Salamina | 0:3 | ||||
| 15. Round | 04/01/2020 | AEK Larnaca | - | Olympiakos Nikosia | 0:0 |  |
|||
| 1. Round | 08/01/2020 | APOEL Nikosia | - | Olympiakos Nikosia | 4:2 | ||||
| 16. Round | 12/01/2020 | Olympiakos Nikosia | - | Apollon Limassol | 0:2 |
Slovakia