Stadium: Court 1 Round: 14 Ground: Clay
| ITF M25 Palmanova | 2023/03/22 10:30 | Diego A B Sanchez v Kai Wehnelt | 7-5,6-3 |
| ITF M25 Palmanova | 2023/03/15 13:00 | Alejandro Manzanera Pertusa v Kai Wehnelt | 6-3,6-3 |
| ITF M25 Palmanova | 2023/03/14 08:00 | Kai Wehnelt v Alvaro Peiro Serrano | 6-1,6-2 |
| ITF M25 Palmanova | 2023/03/13 11:00 | Kai Wehnelt v Axel Herberg Amoros | 6-3,6-3 |
| Challenger Manama | 2023/02/13 09:00 | Mohamed Safwat v Kai Wehnelt | 3-6,7-5,7-5 |
| Challenger Manama | 2023/02/12 13:20 | Mircea-Alexandru Jecan v Kai Wehnelt | 3-6,5-7 |
| Challenger Vilnius | 2023/02/05 14:25 | Daniel Masur v Kai Wehnelt | 3-6,6-4,6-3 |
| ITF M15 Monastir | 2023/01/20 09:00 | Goncalo Oliveira v Kai Wehnelt | 6-2,6-3 |
| Challenger Split | 2023/04/11 12:20 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 |
| ITF M25 Dubrovnik | 2023/04/06 08:00 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 |
| ITF M25 Dubrovnik | 2023/04/05 07:00 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 |
| ITF M25 Toulouse | 2023/03/23 10:00 | Kalin Ivanovski v Harry Wendelken | 1-6,6-7 |
| ITF M25 Toulouse | 2023/03/21 13:00 | Kalin Ivanovski v Paul Inchauspe | 6-2,6-4 |
| ITF M15 Poitiers | 2023/03/18 13:30 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 2-6,6-7 |
| ITF M15 Poitiers | 2023/03/17 15:15 | Tristan Lamasine v Kalin Ivanovski | 5-7,1-6 |
| ITF M15 Poitiers | 2023/03/16 13:15 | Alexandre Reco v Kalin Ivanovski | 6-3,1-6,4-6 |