Stadium: Court 7 Round: 14 Ground: Clay
| 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 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 |
| Davis Cup | 2023/09/15 10:50 | Vladyslav Orlov v Nicolas Mejia | 5-7,6-4,7-6 |
| Davis Cup | 2023/09/14 09:50 | Vladyslav Orlov v Daniel Elahi Galan | 7-5,3-6,0-6 |
| Challenger Istanbul | 2023/09/04 08:30 | Vladyslav Orlov v Blaise Bicknell | 0-6,1-6 |
| Challenger Istanbul | 2023/09/03 11:50 | Vladyslav Orlov v Berk Ilkel | 6-2,6-2 |
| ITF M25 Poznan | 2023/08/23 12:05 | Michal Mikula v Vladyslav Orlov | 2-6,3-6 |
| ITF M25 Bielsko Biala | 2023/08/17 10:30 | Viacheslav Bielinskyi v Vladyslav Orlov | 6-3,6-2 |
| ITF M25 Bielsko Biala | 2023/08/16 10:40 | Fryderyk Lechno-Wasiutynski v Vladyslav Orlov | 6-7,2-6 |
| Challenger Cordenons | 2023/08/08 17:30 | Vladyslav Orlov v Matteo Gigante | 7-6,4-6,4-6 |