Stadium: Court 6 Round: 28 Ground: Hardcourt outdoor
| ITF - M15 Sozopol | 2021/10/15 09:00 | Hazem Naw v Yan Bondarevskiy | 3-6,2-6 |
| ITF - M15 Sozopol | 2021/10/14 15:45 | Yanaki Milev v Yan Bondarevskiy | 3-6,4-6 |
| ITF - M15 Sozopol | 2021/10/13 15:10 | Stefan Palosi v Yan Bondarevskiy | 4-6,6-2,8-10 |
| ITF - M15 Sozopol | 2021/10/09 07:00 | Billy Harris v Yan Bondarevskiy | 6-3,3-6,7-6 |
| ITF - M15 Sozopol | 2021/10/08 07:00 | Yan Bondarevskiy v Alexander Cozbinov | 1-6,6-2,6-1 |
| 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 |
| ITF - M15 Sozopol | 2021/10/15 09:00 | Andrew Paulson v Marko Tepavac | 6-2,6-3 |
| ITF - M15 Sozopol | 2021/10/14 17:15 | Andrew Paulson v Sarp Agabigun | 6-2,6-3 |
| ITF - M15 Sozopol | 2021/10/13 15:40 | Kai Wehnelt v Andrew Paulson | 6-7,1-6 |
| ITF M25 - Praga | 2021/10/07 08:00 | Khumoyun Sultanov v Andrew Paulson | 4-6,6-3,6-2 |
| ITF - M25 Pardubice | 2021/09/23 11:00 | Filip Misolic v Andrew Paulson | 3-6,7-5,6-2 |
| ITF - M25 Pardubice | 2021/09/23 07:30 | Dominik Recek v Andrew Paulson | 2-6,6-7 |
| UTR Pro Tennis Series - Ricany | 2021/09/19 07:00 | Filip Duda v Andrew Paulson | 0-0 |
| UTR Pro Tennis Series - Ricany | 2021/09/18 09:00 | Petr Hajek v Andrew Paulson | 4-6,1-6 |