Stadium: COURT 1 Round: 54 Ground: Hardcourt indoor
| ITF - M15 Sozopol | 2021/09/13 08:00 | Ivan Mikhaylyuk v Richard Biagiotti | 3-6,2-6 |
| UTR Pro Tennis Series - Sofia | 2021/09/02 07:00 | Ivan Mikhaylyuk v George Lazarov | 3-6,1-6 |
| 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 - M15 St Petersburg - Calificari | 2021/04/11 07:00 | Matic Spec v Maksim Starostin | 6-3,6-2 |
| ITF - M15 St Petersburg | 2021/04/04 07:00 | Maxim Ratniuk v Maksim Starostin | 6-4,6-0 |