| 1. Round | 26/08/2019 | Enosis Neon Paralimni | - | Ethnikos Achna | 3:4 |  |
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| 2. Round | 31/08/2019 | AEL Limassol | - | Enosis Neon Paralimni | 2:0 | ||||
| 3. Round | 15/09/2019 | Enosis Neon Paralimni | - | Anorthosis Famagusta | 1:2 | ||||
| 4. Round | 23/09/2019 | Enosis Neon Paralimni | - | APOEL Nikosia | 2:3 | ||||
| 5. Round | 05/10/2019 | Doxa Katokopias | - | Enosis Neon Paralimni | 1:3 |  |
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| 6. Round | 20/10/2019 | Enosis Neon Paralimni | - | Nea Salamina | 0:1 | ||||
| 8. Round | 03/11/2019 | Enosis Neon Paralimni | - | Apollon Limassol | 0:3 | ||||
| 9. Round | 10/11/2019 | Paphos FC | - | Enosis Neon Paralimni | 1:1 | ||||
| 10. Round | 23/11/2019 | Enosis Neon Paralimni | - | Omonia Nikosia | 0:2 | ||||
| 11. Round | 29/11/2019 | Olympiakos Nikosia | - | Enosis Neon Paralimni | 0:0 | |
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| 13. Round | 15/12/2019 | Enosis Neon Paralimni | - | AEL Limassol | 2:2 | ||||
| 15. Round | 05/01/2020 | APOEL Nikosia | - | Enosis Neon Paralimni | 4:0 |
Cyprus