| 1. Round | 18/07/2021 | Mladost Lučani | - | FK Radnički 1923 | 0:1 | ||||
| 4. Round | 06/08/2021 | FK Radnički 1923 | - | Radnik Surdulica | 0:1 | ||||
| 8. Round | 11/09/2021 | FK Radnički 1923 | - | Partizan | 1:3 | ||||
| 14. Round | 24/10/2021 | Vojvodina | - | FK Radnički 1923 | 3:1 | ||||
| 13. Round | 03/11/2021 | Radnički Niš | - | FK Radnički 1923 | 2:1 | ||||
| 19. Round | 06/12/2021 | Radnik Surdulica | - | FK Radnički 1923 | 0:0 | ||||
| 20. Round | 11/12/2021 | FK Radnički 1923 | - | TSC Bačka Topola | 0:3 | ||||
| 21. Round | 15/12/2021 | FK Čukarički | - | FK Radnički 1923 | 2:0 |
Serbia