Stadium: Court 6 Round: 27 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/07 07:00 | Yan Bondarevskiy v Yannik Steinegger | 6-3,6-4 |
| ITF M15 Sozopol | 2021/10/06 06:45 | Yan Bondarevskiy v George Lazarov | 6-7,6-1,6-3 |
| Challenger Sibiu | 2021/09/30 10:40 | Stefano Travaglia v Yan Bondarevskiy | 6-3,6-2 |
| Challenger Sibiu | 2021/09/28 10:45 | Yan Bondarevskiy v Vlad Andrei Dancu | 6-2,6-3 |
| Challenger Sibiu | 2021/09/27 07:00 | Oleg Prihodko v Yan Bondarevskiy | 6-7,4-6 |
| Challenger Sibiu | 2021/09/26 07:30 | Yan Bondarevskiy v David Poljak | 7-5,3-6,6-3 |
| ITF M15 Vyshkovo | 2021/09/21 07:00 | Yan Bondarevskiy v Tommaso Compagnucci | 2-6,7-6,5-7 |
| ITF M15 Zlatibor | 2021/09/18 11:30 | Fabian Marozsan v Yan Bondarevskiy | 6-4,6-3 |
| ITF M15 Sozopol | 2021/10/07 06:50 | Anthony Genov v Alexander Cozbinov | 3-6,1-6 |
| ITF M15 Sozopol | 2021/10/06 09:35 | Martin Dimitrov v Alexander Cozbinov | 1-6,3-6 |
| ITF M25 Skopje | 2021/10/01 12:30 | Alexander Cozbinov v Matteo Arnaldi | 0-6,1-6 |
| ITF M25 Skopje | 2021/10/01 08:15 | Alexander Cozbinov v Stefano Battaglino | 6-2,7-5 |
| ITF M25 Skopje | 2021/09/28 11:15 | Mariano Navone v Alexander Cozbinov | 6-3,5-7,1-6 |
| Challenger Istanbul | 2021/09/12 08:00 | Adrian Andreev v Alexander Cozbinov | 6-4,6-4 |
| ITF M25 Trier | 2021/08/26 09:30 | Tim Handel v Alexander Cozbinov | 6-2,3-6,6-2 |
| ITF M25 Trier | 2021/08/24 15:30 | Alexander Cozbinov v Laurent Lokoli | 6-2,3-6,7-6 |