Stadium: COURT VIKTOR TROICKI Round: 27 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/09/21 09:30 | Yanaki Milev v Erik Arutiunian | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/09/20 08:30 | Yanaki Milev v Aleksa Pisaric | 7-6,6-2 |
| Davis Cup | 2023/09/16 12:40 | Yanaki Milev v Alexander Bublik | 4-6,1-6 |
| Challenger Tulln | 2023/09/03 10:25 | Lukas Rosol v Yanaki Milev | 6-4,6-1 |
| Challenger Prague | 2023/08/20 09:25 | Jakub Nicod v Yanaki Milev | 4-6,6-1,6-2 |
| Challenger Banja Luka | 2023/08/07 15:50 | Akira Santillan v Yanaki Milev | 2-6,6-1,6-3 |
| Challenger Banja Luka | 2023/08/07 11:45 | Drazen Petrovic v Yanaki Milev | 3-6,4-6 |
| Challenger Liberec | 2023/07/31 11:05 | Michael Vrbensky v Yanaki Milev | 6-4,6-2 |
| ITF M15 Kursumlijska Banja | 2023/09/21 09:05 | Viktor Jovic v Petr Nesterov | 5-7,6-2,5-7 |
| ITF M15 Kursumlijska Banja | 2023/09/20 07:00 | Shendrit Deari v Petr Nesterov | 0-6,4-6 |
| UTR Pro Sofia | 2023/09/10 07:00 | Petr Nesterov v Gabriel Donev | 7-6,3-0 |
| UTR Pro Sofia | 2023/09/09 06:30 | Petr Nesterov v Nicolas Buitrago | 6-4,6-3 |
| UTR Pro Sofia | 2023/09/08 06:30 | Christos Antonopoulos v Petr Nesterov | 6-7,4-6 |
| UTR Pro Sofia | 2023/09/07 08:00 | Wadym Konowczuk v Petr Nesterov | 6-3,0-6,2-6 |
| UTR Pro Sofia | 2023/09/06 05:00 | Mert Ramadan v Petr Nesterov | 4-6,4-6 |
| UTR Pro Sofia | 2023/09/04 08:00 | Enrique Bogo v Petr Nesterov | 3-6,4-6 |