Stadium: Court 8 Round: 25 Ground: Clay
| Challenger Sibiu | 2023/09/18 07:00 | Filip Cristian Jianu v Kai Wehnelt | 6-0,7-5 |
| Challenger Sibiu | 2023/09/17 08:55 | Kai Wehnelt v Vladyslav Orlov | 7-5,6-7,6-4 |
| Challenger Szczecin | 2023/09/10 14:20 | Rudolf Molleker v Kai Wehnelt | 6-4,7-5 |
| Challenger Tulln | 2023/09/03 08:00 | Kai Wehnelt v Jeremy Jahn | 4-6,4-6 |
| 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 M15 Arad | 2023/09/25 07:00 | Jan Kupcic v Samuil Konov | 7-6,4-6,10-6 |
| ITF M25 Maribor | 2023/09/06 09:50 | Jan Kupcic v Mathys Erhard | 6-4,1-6,4-6 |
| ITF M25 Maribor | 2023/08/31 08:50 | Jan Kupcic v Mirza Basic | 4-6,6-7 |
| ITF M15 Kottingbrunn | 2023/08/13 12:00 | Jan Kupcic v Dennis Dragomirov | 4-6,6-7 |
| ITF M25 Osijek | 2023/08/09 12:25 | Jan Kupcic v Luca Giacomini | 6-2,2-6,3-6 |
| ITF M15 Novi Sad | 2023/07/30 08:30 | Miha Vetrih v Jan Kupcic | 6-7,6-4,10-8 |
| ITF M15 Novi Sad | 2023/07/25 07:30 | Tom Paris v Jan Kupcic | 6-2,6-3 |
| ITF M15 Novi Sad | 2023/07/24 07:30 | Marcell Bartakovics v Jan Kupcic | 4-6,4-6 |