Stadium: Court 2 Round: 14 Ground: Clay
| Challenger Hamburg | 2022/10/17 09:00 | Kai Wehnelt v Jeremy Jahn | 6-7,6-7 |
| ITF M25 Poznan | 2023/08/26 09:00 | Kai Wehnelt v Georgii Kravchenko | 2-6,5-7 |
| ITF M25 Poznan | 2023/08/25 09:00 | Kai Wehnelt v Sander Jong | 7-6,6-3 |
| ITF M25 Poznan | 2023/08/24 09:00 | Maks Kasnikowski v Kai Wehnelt | 4-6,4-6 |
| ITF M25 Poznan | 2023/08/23 12:45 | Siim Troost v Kai Wehnelt | 7-6,0-6,0-6 |
| ITF M25 Koksijde | 2023/08/14 12:00 | Kai Wehnelt v Luciano Emanuel Ambrogi | 3-6,3-6 |
| Challenger Meerbusch | 2023/08/07 10:00 | Georgii Kravchenko v Kai Wehnelt | 6-4,7-6 |
| Challenger Luedenscheid | 2023/07/31 15:25 | Duje Ajdukovic v Kai Wehnelt | 6-4,3-6,6-3 |
| Challenger Luedenscheid | 2023/07/30 12:05 | Kai Wehnelt v Jose Pereira | 6-2,6-4 |
| ITF M25 Oldenzaal | 2023/09/01 16:00 | Jeremy Jahn v Max Houkes | 3-6,6-7 |
| ITF M25 Oldenzaal | 2023/08/31 08:00 | Jeremy Jahn v Marlon Vankan | 7-6,6-2 |
| ITF M25 Oldenzaal | 2023/08/29 12:20 | Alec Deckers v Jeremy Jahn | 6-3,4-6,6-7 |
| ITF M25 Poznan | 2023/08/25 11:00 | Jeremy Jahn v Viacheslav Bielinskyi | 6-0,4-6,2-6 |
| ITF M25 Poznan | 2023/08/24 11:05 | Jeremy Jahn v Jasza Szajrych | 6-2,7-6 |
| ITF M25 Poznan | 2023/08/23 14:05 | Jeremy Jahn v Dominik Kellovsky | 7-5,6-4 |
| ITF M25 Koksijde | 2023/08/19 14:00 | Timo Legout v Jeremy Jahn | 3-6,7-5,6-4 |
| ITF M25 Koksijde | 2023/08/18 11:25 | Jeremy Jahn v Marlon Vankan | 6-4,6-1 |