Stadium: Court 8 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/13 09:00 | Yanaki Milev v Romios, Matthew Christopher | 2-6,7-5,15-13 |
| ITF M15 Sozopol | 2021/09/14 14:00 | Yanaki Milev v Apostol, Bogdan Ionut | 6-7,6-7 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Milushev, Plamen | 3-6,6-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 09:00 | Dzhavakian, Yurii v Yanaki Milev | 4-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 06:00 | Kirkov, Vasil v Yanaki Milev | 6-1,6-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 09:00 | Gorazd Srbljak v Yanaki Milev | 6-3,6-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 10:30 | Vladimir Popov v Yanaki Milev | 4-6,6-4,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 06:00 | Yanaki Milev v Aleksandr Braynin | 7-6,4-6,4-6 |
| ITF M15 Sozopol | 2021/10/13 15:10 | Stefan Palosi v Bondarevskiy, Yan | 4-6,6-2,8-10 |
| ITF M15 Sozopol | 2021/10/09 07:00 | Billy Harris v Bondarevskiy, Yan | 6-3,3-6,7-6 |
| ITF M15 Sozopol | 2021/10/08 07:00 | Bondarevskiy, Yan v Cozbinov, Alexander | 1-6,6-2,6-1 |
| ITF M15 Sozopol | 2021/10/07 07:00 | Bondarevskiy, Yan v Yannik Steinegger | 6-3,6-4 |
| ITF M15 Sozopol | 2021/10/06 06:45 | Bondarevskiy, Yan v George Lazarov | 6-7,6-1,6-3 |
| Challenger Sibiu | 2021/09/30 10:40 | Stefano Travaglia v Bondarevskiy, Yan | 6-3,6-2 |
| Challenger Sibiu | 2021/09/28 10:45 | Bondarevskiy, Yan v Vlad Andrei Dancu | 6-2,6-3 |
| Challenger Sibiu | 2021/09/27 07:00 | Oleg Prihodko v Bondarevskiy, Yan | 6-7,4-6 |