Stadium: Court 1 Round: 25 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/09/19 10:55 | Martin Zeljenka v Tadija Radovanovic | 5-7,7-6,9-11 |
| ITF M15 Kursumlijska Banja | 2023/09/18 07:00 | Tadija Radovanovic v Adrian Arcon | 6-4,6-3 |
| ITF M15 Kursumlijska Banja | 2023/09/17 08:30 | Tadija Radovanovic v Oskari Eerola | 5-7,7-5,10-8 |
| UTR Pro Sofia | 2023/09/10 05:00 | Tadija Radovanovic v Christos Antonopoulos | 6-4,4-6,0-6 |
| UTR Pro Sofia | 2023/09/09 08:00 | Milen Ianakiev v Tadija Radovanovic | 4-6,3-6 |
| UTR Pro Sofia | 2023/09/07 05:00 | Tadija Radovanovic v Nicolas Buitrago | 1-6,5-7 |
| UTR Pro Sofia | 2023/09/06 06:30 | Tadija Radovanovic v Rayane Oumaouche | 2-6,5-7 |
| UTR Pro Sofia | 2023/09/05 08:00 | Tadija Radovanovic v Vardan Manukyan | 2-6,6-4,6-4 |
| ITF M15 Kursumlijska Banja | 2023/09/15 07:55 | Stefan Popovic v Svyatoslav Gulin | 5-7,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/14 11:40 | Stefan Popovic v Romeo Hadzimehmedovic | 6-2,6-3 |
| ITF M15 Kursumlijska Banja | 2023/09/12 10:40 | Stefan Popovic v Jacques-Kai Inoue | 6-1,7-6 |
| ITF M25 Maribor | 2023/09/06 09:30 | Bor Artnak v Stefan Popovic | 6-3,6-1 |
| ITF M25 Maribor | 2023/08/31 14:25 | Stefan Popovic v Raphael Calzi | 7-6,6-2 |
| ITF M25 Maribor | 2023/08/31 09:50 | Filip Cristian Jianu v Stefan Popovic | 5-7,4-6 |
| Challenger Banja Luka | 2023/08/07 16:00 | Miljan Zekic v Stefan Popovic | 6-3,6-0 |
| Challenger Banja Luka | 2023/08/07 12:20 | Stefan Popovic v Neil Oberleitner | 6-4,6-2 |