| 7. Round | 19/10/2020 | Olympiakos Nikosia | - | Apollon Limassol | 0:1 | ||||
| 10. Round | 08/11/2020 | Olympiakos Nikosia | - | Nea Salamina | 0:0 | ||||
| 13. Round | 05/12/2020 | AEK Larnaca | - | Olympiakos Nikosia | 4:0 | ||||
| 16. Round | 24/12/2020 | Doxa Katokopias | - | Olympiakos Nikosia | 1:1 | ||||
| 18. Round | 07/01/2021 | Paphos FC | - | Olympiakos Nikosia | 5:0 | ||||
| 20. Round | 17/01/2021 | Apollon Limassol | - | Olympiakos Nikosia | 2:1 | ||||
| 15. Round | 20/01/2021 | Olympiakos Nikosia | - | Enosis Neon Paralimni | 0:1 | ||||
| 21. Round | 23/01/2021 | Olympiakos Nikosia | - | Ethnikos Achna | 1:2 |  |
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| 22. Round | 29/01/2021 | Omonia Nikosia | - | Olympiakos Nikosia | 1:1 | ||||
| 23. Round | 05/02/2021 | Nea Salamina | - | Olympiakos Nikosia | 1:2 | ||||
| 25. Round | 14/02/2021 | Karmiotissa Polemidion | - | Olympiakos Nikosia | 0:3 |
Bulgaria