| ITF M15 Sozopol | 2021/10/14 15:45 | Yanaki Milev v Yan Bondarevskiy | 3-6,4-6 |
| ITF M15 Sozopol | 2021/10/13 09:00 | Yanaki Milev v Matthew Romios | 2-6,7-5,15-13 |
| ITF M15 Sozopol | 2021/09/14 14:00 | Yanaki Milev v Bogdan Ionut Apostol | 6-7,6-7 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 09:00 | Yurii Dzhavakian v Yanaki Milev | 4-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 06:00 | Vasil Kirkov 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 |
| ITF M15 Heraklion | 2021/11/17 11:20 | Kai Wehnelt v Simon A Ivanov | 5-7,4-6 |
| ITF M15 Heraklion | 2021/11/16 07:00 | Simon A Ivanov v Gianluca Coloma-Heck | 6-1,6-2 |
| ITF M15 Heraklion | 2021/11/15 08:00 | Simon A Ivanov v Thomas George Brun | 6-2,6-0 |
| ITF M15 Heraklion | 2021/11/10 08:30 | Simon A Ivanov v Michael Weindl | 7-5,1-6,1-6 |
| UTR Pro Tennis Series Brasov | 2021/10/30 09:30 | Vasile Antonescu v Simon A Ivanov | 6-0,6-3 |
| UTR Pro Tennis Series Brasov | 2021/10/27 11:30 | Simon A Ivanov v Bogdan Borza | 4-6,2-5 |
| UTR Pro Tennis Series Brasov | 2021/10/26 07:00 | Simon A Ivanov v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/25 08:30 | Simon A Ivanov v Samuil Konov | 6-4,6-2 |