Stadium: Court 7 Round: 44 Ground: Hardcourt outdoor
| 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 M25 - Belgrad | 2021/06/27 07:00 | Dusan Rajic v Ivan Mikhaylyuk | 2-6,6-0,12-10 |
| ITF M15 - Sozopol | 2021/09/12 11:00 | Sergo Sikharulidze v Richard Biagiotti | 6-4,5-7,6-10 |
| ITF M15 - Pescara | 2021/08/15 11:15 | Maxence Broville v Richard Biagiotti | 6-1,7-6 |
| ITF M15 - Vejle | 2021/07/25 09:00 | Oscar Moraing v Richard Biagiotti | 6-3,6-2 |