| UTR Pro Sofia | 2023/09/08 05:00 | Gabriel Donev v Milen Ianakiev | 6-3,5-2 |
| UTR Pro Sofia | 2023/09/07 06:30 | Janos Fekete v Milen Ianakiev | 7-5,5-3 |
| UTR Pro Sofia | 2023/09/06 05:00 | Sergo Sikharulidze v Milen Ianakiev | 6-4,4-6,2-6 |
| UTR Pro Sofia | 2023/09/04 07:04 | Christos Keisidis v Milen Ianakiev | 3-6,5-7 |
| UTR Pro Tennis Series Sofia | 2021/09/02 13:45 | Mihael Mihaylov v Milen Ianakiev | 6-4,3-6,5-2 |
| UTR Pro Tennis Series Sofia | 2021/09/01 09:30 | Milen Ianakiev v Julien De Cuyper | 6-3,5-1 |
| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Milen Ianakiev v Alexander Lazov | 6-7,2-6 |
| UTR Pro Tennis Series Sofia | 2021/08/30 08:30 | Milen Ianakiev v Yurii Dzhavakian | 4-6,2-6 |
| 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 |
| ITF M15 Belgrade | 2023/06/25 09:30 | Nikola Puric v Tadija Radovanovic | 6-4,3-6,10-7 |