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| 25/09/2019 | 14:30 | FK Sinđelić Beograd | - | FK Zemun | 4:2 pso | |
| 14:30 | Budućnost Dobanovci | - | Radnički Niš | 1:4 (1:3) | ||
| 14:30 | FK Napredak | - | TSC Bačka Topola | 3:4 (0:1, 1:1, 1:1) pso | ||
| 14:30 | FK Zlatibor | - | Vojvodina | 1:4 (0:2) | ||
| 14:30 | FK Inđija | - | Dinamo Vranje | 2:0 (2:0) | ||
| 14:30 | OFK Beograd | - | FK Rad Beograd | 3:2 (2:1) | ||
| 14:30 | FK Bratstvo 1946 | - | Mladost Lučani | 1:3 (0:2) | ||
| 16:00 | OFK Bačka | - | FK Radnički 1923 | 1:0 (0:0) | ||
| 17:00 | Mačva Šabac | - | FK Metalac | 1:0 (1:0) | ||
| 17:00 | FK Čukarički | - | FK Žarkovo | 3:1 (3:0) | ||
| 18:00 | Spartak Subotica | - | FK Novi Pazar | 2:0 (1:0) | ||
| 26/09/2019 | 14:30 | FK Trayal | - | Radnik Surdulica | 2:3 (1:2) | |
| 09/10/2019 | 14:00 | FK Vodojaža | - | Partizan | 0:6 (0:1) | |
| 14:00 | Proleter Novi Sad | - | FK Javor | 2:1 (0:1) | ||
| 14:00 | FK Voždovac | - | Teleoptik Zemun | 7:8 (0:1, 2:2, 2:2) pso | ||
| 10/10/2019 | 14:00 | FK Trepča | - | Crvena Zvezda | 0:8 (0:2) |
