Stadium: Court 7 Round: 14 Ground: Clay
| ITF M15 Nyiregyhaza | 2023/06/07 08:00 | Peter Nad v Kai Wehnelt | 6-4,1-6,6-3 |
| ITF M25 Reggio Emilia | 2023/05/19 09:00 | Julian Ocleppo v Kai Wehnelt | 6-4,3-6,6-2 |
| ITF M25 Reggio Emilia | 2023/05/17 10:00 | Gian Marco Ortenzi v Kai Wehnelt | 0-6,2-6 |
| ITF M25 Reggio Emilia | 2023/05/15 16:30 | Kai Wehnelt v Federico Marchetti | 6-1,6-0 |
| ITF M25 Reggio Emilia | 2023/05/15 09:50 | Kai Wehnelt v Noah Perfetti | 6-3,3-6,10-6 |
| Challenger Francavilla | 2023/05/07 16:40 | Stefano Travaglia v Kai Wehnelt | 6-4,6-2 |
| ITF M25 Santa Margherita | 2023/05/01 11:00 | Sebastian Fanselow v Kai Wehnelt | 4-6,7-6,6-3 |
| ITF M25 Santa Margherita | 2023/04/24 10:40 | Kai Wehnelt v Andrey Chepelev | 3-6,4-6 |
| ATP Stuttgart | 2023/06/10 12:30 | Vladyslav Orlov v Antoine Bellier | 3-6,4-6 |
| Challenger Heilbronn | 2023/06/05 10:30 | Sebastian Fanselow v Vladyslav Orlov | 6-3,3-6,6-3 |
| Challenger Heilbronn | 2023/06/04 10:55 | Petros Tsitsipas v Vladyslav Orlov | 2-6,4-6 |
| Challenger Troisdorf | 2023/05/28 08:30 | Marvin Moeller v Vladyslav Orlov | 6-1,6-3 |
| ITF M25 Bodrum | 2023/05/25 07:00 | Vladyslav Orlov v George Loffhagen | 4-6,2-6 |
| ITF M25 Bodrum | 2023/05/24 07:30 | Vladyslav Orlov v Sarp Agabigun | 6-1,6-1 |
| ITF M25 Bodrum | 2023/05/23 08:20 | Vladyslav Orlov v Aleksandre Metreveli | 6-3,6-0 |
| ITF M25 Valldoreix | 2023/05/09 11:25 | David Jorda Sanchis v Vladyslav Orlov | 6-4,3-6,6-3 |