| 1. Round | 24/08/2019 | Doxa Katokopias | - | Omonia Nikosia | 0:2 | ||||
| 2. Round | 01/09/2019 | Olympiakos Nikosia | - | Doxa Katokopias | 1:1 | ||||
| 3. Round | 15/09/2019 | Doxa Katokopias | - | Ethnikos Achna | 1:1 | ||||
| 4. Round | 21/09/2019 | AEL Limassol | - | Doxa Katokopias | 1:0 |  |
|||
| 5. Round | 05/10/2019 | Doxa Katokopias | - | Enosis Neon Paralimni | 1:3 | ||||
| 6. Round | 19/10/2019 | APOEL Nikosia | - | Doxa Katokopias | 2:0 | ||||
| 7. Round | 27/10/2019 | Doxa Katokopias | - | Anorthosis Famagusta | 0:6 | ||||
| 10. Round | 25/11/2019 | Doxa Katokopias | - | Apollon Limassol | 0:1 | ||||
| 11. Round | 01/12/2019 | Paphos FC | - | Doxa Katokopias | 0:1 | ||||
| 13. Round | 13/12/2019 | Doxa Katokopias | - | Olympiakos Nikosia | 2:6 | |
|||
| 14. Round | 22/12/2019 | Ethnikos Achna | - | Doxa Katokopias | 1:1 | ||||
| 15. Round | 03/01/2020 | Doxa Katokopias | - | AEL Limassol | 2:2 | |
|||
| 17. Round | 25/01/2020 | Doxa Katokopias | - | APOEL Nikosia | 0:3 | |
|||
| 18. Round | 01/02/2020 | Anorthosis Famagusta | - | Doxa Katokopias | 3:0 | |
|||
| 19. Round | 10/02/2020 | Nea Salamina | - | Doxa Katokopias | 0:1 | ||||
| 20. Round | 16/02/2020 | Doxa Katokopias | - | AEK Larnaca | 0:1 | ||||
| 21. Round | 22/02/2020 | Apollon Limassol | - | Doxa Katokopias | 3:2 |
North Macedonia