Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger Sibiu | 2021/09/27 07:00 | Kai Wehnelt v Stefan Palosi | 6-7,7-6,2-6 |
| ITF M15 Sozopol | 2021/09/19 07:00 | Kai Wehnelt v Ryan James Storrie | 4-6,6-0,2-6 |
| ITF M15 Sozopol | 2021/09/18 07:00 | Kai Wehnelt v Martin Krumich | 6-4,6-2 |
| ITF M15 Sozopol | 2021/09/17 07:00 | Kai Wehnelt v Calin Manda | 4-6,6-4,6-1 |
| ITF M15 Sozopol | 2021/09/16 07:00 | Kai Wehnelt v Joshua Paris | 6-2,6-4 |
| ITF M15 Sozopol | 2021/09/14 09:00 | Kai Wehnelt v Zura Tkemaladze | 6-2,6-2 |
| ITF M25 Eupen | 2021/09/08 07:30 | Guy Den Heijer v Kai Wehnelt | 3-6,6-3,6-2 |
| ITF M25 Trier | 2021/08/26 11:00 | Quentin Folliot v Kai Wehnelt | 7-5,4-6,7-5 |
| ITF M15 Sozopol | 2021/09/13 08:00 | Nikolay Nedelchev v Dian Nedev | 6-3,6-1 |
| UTR Pro Tennis Series Sofia | 2021/09/03 07:00 | Alexander Lazov v Dian Nedev | 7-5,5-3 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Martin Dimitrov v Dian Nedev | 3-6,3-5 |
| UTR Pro Tennis Series Sofia | 2021/09/01 08:00 | Dian Nedev v Alexandar Lazarov | 1-6,4-6 |
| UTR Pro Tennis Series Sofia | 2021/08/31 08:00 | Dian Nedev v Ivailo Keremedchiev | 6-4,5-2 |
| UTR Pro Tennis Series Sofia | 2021/08/30 08:30 | Plamen Milushev v Dian Nedev | 4-6,2-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 07:30 | Aleksandr Braynin v Dian Nedev | 6-3,6-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 10:30 | Dian Nedev v Ilya Snitari | 4-6,6-4,1-6 |