| 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 |
| UTR Pro Sofia | 2023/09/04 05:00 | Tadija Radovanovic v Anthony Turchi | 6-0,4-6,6-4 |
| ITF M15 Novi Sad | 2023/07/31 09:30 | Nicolas Bruna v Tadija Radovanovic | 6-4,6-4 |
| ITF M15 Novi Sad | 2023/07/24 11:55 | Tadija Radovanovic v Zak Talic | 6-4,2-6,2-10 |
| ITF M15 Novi Sad | 2023/07/23 13:00 | Dmitrii Vasilev v Tadija Radovanovic | 0-6,4-6 |
| UTR Pro Sofia | 2023/09/09 05:00 | Christos Antonopoulos v Aniss Rafiq | 6-2,7-5 |
| UTR Pro Sofia | 2023/09/08 06:30 | Christos Antonopoulos v Petr Nesterov | 6-7,4-6 |
| UTR Pro Sofia | 2023/09/07 05:00 | Christos Antonopoulos v Enrique Bogo | 3-6,2-6 |
| UTR Pro Sofia | 2023/09/06 08:00 | Wadym Konowczuk v Christos Antonopoulos | 3-6,1-6 |
| UTR Pro Sofia | 2023/09/05 05:00 | Mert Ramadan v Christos Antonopoulos | 7-6,1-6,1-6 |
| ITF M25 Skopje | 2023/06/06 07:30 | Davud Amirov v Christos Antonopoulos | 6-4,6-7,10-4 |
| ITF M25 Skopje | 2023/06/05 12:15 | Aleksa Smiljanic v Christos Antonopoulos | 3-6,2-6 |
| ITF M25 Skopje | 2023/06/04 09:30 | Ivo Vercik v Christos Antonopoulos | 2-6,1-6 |