| UTR Pro - Belgrado | 2023/10/02 12:35 | Vuk Radjenovic v Obrad Markovski | 6-2,3-6,6-4 |
| UTR Pro - Belgrado | 2023/10/01 10:30 | Vuk Radjenovic v Karlo Kajin | 6-2,6-3 |
| ITF - M25 Zlatibor | 2023/09/27 12:30 | Erik Arutiunian v Vuk Radjenovic | 5-7,7-5,10-7 |
| ITF - M25 Zlatibor | 2023/09/27 07:00 | Adrian Arcon v Vuk Radjenovic | 6-3,3-6,4-10 |
| ITF - M25 Zlatibor | 2023/09/26 09:30 | Aleksa Smiljanic v Vuk Radjenovic | 1-6,2-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/19 10:35 | Vuk Radjenovic v Luka Pavlovic | 3-6,3-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/14 09:30 | Vuk Radjenovic v Aldin Setkic | 1-6,3-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/12 10:10 | Klim Kozyrev v Vuk Radjenovic | 0-6,3-6 |
| UTR Pro - Belgrado | 2023/10/02 13:41 | Karlo Kajin v Milan Drinic | 3-6,6-0,6-2 |
| UTR Pro - Belgrado | 2023/10/01 09:43 | Milan Drinic v Obrad Markovski | 2-6,5-7 |
| ITF - M15 Kuršumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| ITF - M15 Pirot | 2023/09/05 12:55 | Filip Cristian Jianu v Milan Drinic | 4-6,6-4,6-4 |
| ITF - M15 Kuršumlijska Banja | 2023/08/30 10:30 | Milan Drinic v Peter Fajta | 3-6,6-3,6-7 |
| ITF - M25 Osijek | 2023/08/10 09:45 | Milan Drinic v Sebastian Prechtel | 5-7,7-6,2-6 |
| ITF - M25 Osijek | 2023/08/08 10:55 | Viktor Jovic v Milan Drinic | 2-6,3-6 |