| UTR Pro Tennis Series Sofia | 2021/09/01 09:30 | Tadija Radovanovic v Ivan Mikhaylyuk | 2-6,6-3,4-6 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Leonid Sheyngezikht v Ivan Mikhaylyuk | 6-2,7-5 |
| UTR Pro Tennis Series Sofia | 2021/08/30 10:00 | Alexandru Luca v Ivan Mikhaylyuk | 2-6,2-6 |
| ITF M15 Sofia | 2021/07/05 13:30 | Ivan Mikhaylyuk v Andrew Fenty | 3-6,6-7 |
| ITF M15 Sofia | 2021/07/05 08:00 | Christoffer Solberg v Ivan Mikhaylyuk | 1-6,3-6 |
| ITF M15 Sofia | 2021/07/04 10:30 | Andrea Del Federico v Ivan Mikhaylyuk | 2-6,5-7 |
| ITF M25 Belgrade | 2021/06/27 07:00 | Dusan Rajic v Ivan Mikhaylyuk | 2-6,6-0,12-10 |
| ITF M15 Sharm El Sheikh | 2021/04/06 09:15 | Volodymyr Uzhylovskyi v Ivan Mikhaylyuk | 6-3,7-5 |
| UTR Pro Tennis Series Sofia | 2021/09/01 06:30 | Volodymyr Uzhylovskyi v George Lazarov | 1-6,6-1,1-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Valentin Vanta v George Lazarov | 6-4,6-0 |
| UTR Pro Tennis Series Sofia | 2021/08/30 12:00 | Warren Sinius v George Lazarov | 2-6,2-5 |
| UTR Pro Tennis Series Sofia | 2021/08/29 12:00 | George Lazarov v Mario Radev | 6-0,6-1 |