| UTR Pro Tennis Series - Plovdiv | 2022/02/11 09:00 | Ioan Alexandru Chirita v Yanaki Milev | 6-7,2-6 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/10 10:21 | Oleksandr Bielinskyi v Yanaki Milev | 6-3,5-2 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/08 09:54 | Gabriel Donev v Yanaki Milev | 6-4,1-6,6-3 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/07 10:30 | Yanaki Milev v Alexander Lazov | 7-5,5-3 |
| ITF - M15 - Antalya | 2022/01/28 13:15 | Yanaki Milev v S Mert Ozdemir | 7-5,3-6,7-10 |
| ITF - M15 - Antalya | 2022/01/28 08:00 | Paul Woerner v Yanaki Milev | 6-3,4-6,10-8 |
| ITF - M15 - Antalya | 2022/01/27 09:00 | Cedric Stanke v Yanaki Milev | 4-6,3-6 |
| ITF - M15 Sozopol | 2021/10/14 15:45 | Yanaki Milev v Yan Bondarevskiy | 3-6,4-6 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/10 11:52 | Simon A Ivanov v Gorazd Srbljak | 4-6,5-7 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/09 10:30 | Simon A Ivanov v Yurii Dzhavakian | 7-5,6-2 |
| UTR Pro Tennis Series - Plovdiv | 2022/02/07 09:00 | Simon A Ivanov v George Lazarov | 6-3,3-6,6-3 |
| ITF - M25 Cairo | 2022/01/27 09:00 | Lukas Krainer v Simon A Ivanov | 4-6,6-3,6-1 |
| ITF - M25 Cairo | 2022/01/26 11:05 | Simon A Ivanov v Denis Klok | 2-6,6-3,7-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/15 10:00 | Simon A Ivanov v Kuzey Cekirge | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/13 09:30 | Vladimir Popov v Simon A Ivanov | 6-2,3-6,1-6 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/05 09:30 | Simon A Ivanov v Edris Fetisleam | 3-6,4-6 |