Stadium: Court 21 Round: 25 Ground: Hardcourt outdoor
| ITF - Villers Les Nancy M25 | 2021/11/09 10:50 | Tristan Schoolkate v Kai Wehnelt | 7-5,6-2 |
| ITF - Hamburg M25 | 2021/10/21 09:55 | Louis Wessels v Kai Wehnelt | 7-5,4-6,6-3 |
| ITF - Hamburg M25 | 2021/10/20 08:00 | Kai Wehnelt v Markus Eriksson | 6-4,7-5 |
| ITF - Sozopol M15 | 2021/10/13 15:40 | Kai Wehnelt v Andrew Paulson | 6-7,1-6 |
| ITF - Sozopol M15 | 2021/10/10 07:00 | Billy Harris v Kai Wehnelt | 6-4,6-1 |
| ITF - Sozopol M15 | 2021/10/09 07:00 | Alexander Donski v Kai Wehnelt | 6-4,3-6,6-7 |
| ITF - Sozopol M15 | 2021/10/08 07:00 | Kai Wehnelt v Ilya Snitari | 7-6,6-3 |
| ITF - Sozopol M15 | 2021/10/07 07:00 | Kai Wehnelt v George Tsivadze | 6-3,6-1 |
| ITF - Heraklion M15 | 2021/11/16 07:00 | Simon A Ivanov v Gianluca Coloma-Heck | 6-1,6-2 |
| ITF - Heraklion M15 | 2021/11/15 08:00 | Simon A Ivanov v Thomas George Brun | 6-2,6-0 |
| ITF - Heraklion M15 | 2021/11/10 08:30 | Simon A Ivanov v Michael Weindl | 7-5,1-6,1-6 |
| UTR Pro Tennis Series - Brasov | 2021/10/30 09:30 | Vasile Antonescu v Simon A Ivanov | 6-0,6-3 |
| UTR Pro Tennis Series - Brasov | 2021/10/27 11:30 | Simon A Ivanov v Bogdan Borza | 4-6,2-5 |
| UTR Pro Tennis Series - Brasov | 2021/10/26 07:00 | Simon A Ivanov v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series - Brasov | 2021/10/25 08:30 | Simon A Ivanov v Samuil Konov | 6-4,6-2 |
| ITF - Sozopol M15 | 2021/10/13 10:00 | Simon A Ivanov v Petr Nesterov | 3-6,2-6 |