| 1. Round | 18/08/2019 | Drita Gjilan | - | KF Ferizaj | 0:1 |  |
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| 3. Round | 31/08/2019 | KF Dukagjini | - | Drita Gjilan | 0:4 | ||||
| 4. Round | 14/09/2019 | Drita Gjilan | - | KF Feronikeli | 1:0 | ||||
| 5. Round | 18/09/2019 | KF Llapi | - | Drita Gjilan | 2:2 |  |
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| 6. Round | 22/09/2019 | Drita Gjilan | - | KF Trepça'89 | 1:1 | |
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| 7. Round | 29/09/2019 | KF Gjilani | - | Drita Gjilan | 0:1 | ||||
| 8. Round | 03/10/2019 | Drita Gjilan | - | FC Vushtrria | 5:1 | ||||
| 9. Round | 08/10/2019 | FK Drenica | - | Drita Gjilan | 1:1 | |
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| 10. Round | 20/10/2019 | Drita Gjilan | - | KF Ballkani | 2:0 | |
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| 11. Round | 24/10/2019 | KF Prishtina | - | Drita Gjilan | 1:0 | ||||
| 13. Round | 03/11/2019 | KF Flamurtari | - | Drita Gjilan | 1:0 | |
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| 14. Round | 06/11/2019 | Drita Gjilan | - | KF Dukagjini | 1:0 | ||||
| 16. Round | 23/11/2019 | Drita Gjilan | - | KF Llapi | 2:0 | ||||
| 17. Round | 01/12/2019 | KF Trepça'89 | - | Drita Gjilan | 3:1 | |
Brazil