| 2. Round | 24/08/2019 | KF Ferizaj | - | KF Gjilani | 0:3 | ||||
| 3. Round | 01/09/2019 | KF Gjilani | - | FC Vushtrria | 2:0 | ||||
| 4. Round | 14/09/2019 | FK Drenica | - | KF Gjilani | 0:2 | ||||
| 5. Round | 18/09/2019 | KF Gjilani | - | KF Ballkani | 1:0 | ||||
| 15. Round | 10/11/2019 | KF Gjilani | - | FK Drenica | 1:1 | ||||
| 16. Round | 22/11/2019 | KF Ballkani | - | KF Gjilani | 2:1 | ||||
| 18. Round | 16/02/2020 | Drita Gjilan | - | KF Gjilani | 2:0 |  |
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| 19. Round | 23/02/2020 | KF Gjilani | - | KF Flamurtari | 2:0 | ||||
| 21. Round | 04/03/2020 | KF Gjilani | - | KF Feronikeli | 2:1 | ||||
| 22. Round | 08/03/2020 | KF Llapi | - | KF Gjilani | 2:1 | ||||
| 26. Round | 24/06/2020 | KF Dukagjini | - | KF Gjilani | 1:3 | ||||
| 27. Round | 29/06/2020 | KF Gjilani | - | KF Llapi | 2:2 | ||||
| 29. Round | 08/07/2020 | KF Gjilani | - | KF Prishtina | 2:1 | ||||
| 30. Round | 12/07/2020 | KF Gjilani | - | FK Drenica | 2:0 | ||||
| 31. Round | 18/07/2020 | Drita Gjilan | - | KF Gjilani | 0:2 |
Kosovo