| 8. Round | 03/11/2019 | Anorthosis Famagusta | - | Olympiakos Nikosia | 4:0 | ||||
| 9. Round | 10/11/2019 | Olympiakos Nikosia | - | Ethnikos Achna | 4:0 |  |
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| 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 | ||||
| 15. Round | 04/01/2020 | AEK Larnaca | - | Olympiakos Nikosia | 0:0 | |
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| 1. Round | 08/01/2020 | APOEL Nikosia | - | Olympiakos Nikosia | 4:2 | ||||
| 17. Round | 25/01/2020 | Paphos FC | - | Olympiakos Nikosia | 1:1 |
Cameroon