Stadium: COURT 1 Round: 54 Ground: Hardcourt indoor
| ITF M15 Sozopol | 2021/09/13 08:00 | Mikhaylyuk, Ivan v Richard Biagiotti | 3-6,2-6 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Mikhaylyuk, Ivan v George Lazarov | 3-6,1-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 09:30 | Tadija Radovanovic v Mikhaylyuk, Ivan | 2-6,6-3,4-6 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Leonid Sheyngezikht v Mikhaylyuk, Ivan | 6-2,7-5 |
| UTR Pro Tennis Series Sofia | 2021/08/30 10:00 | Alexandru Luca v Mikhaylyuk, Ivan | 2-6,2-6 |
| ITF M15 Sofia | 2021/07/05 13:30 | Mikhaylyuk, Ivan v Andrew Fenty | 3-6,6-7 |
| ITF M15 Sofia | 2021/07/05 08:00 | Solberg, Christoffer v Mikhaylyuk, Ivan | 1-6,3-6 |
| ITF M15 Sofia | 2021/07/04 10:30 | Del Federico, Andrea v Mikhaylyuk, Ivan | 2-6,5-7 |
| ITF M15 St Petersburg Qual | 2021/04/11 07:00 | Spec, Matic v Maksim Starostin | 6-3,6-2 |
| ITF M15 St Petersburg | 2021/04/04 07:00 | Ratniuk, Maxim v Maksim Starostin | 6-4,6-0 |