Stadium: Court 14 Round: 14 Ground: Hardcourt outdoor
| Challenger Karlsruhe | 2023/07/06 09:00 | Rudolf Molleker v Ivan Gakhov | 4-6,6-3,3-6 |
| Challenger Maspalomas | 2023/11/29 12:00 | Jonas Forejtek v Ivan Gakhov | 2-6,6-4,6-3 |
| Challenger Maspalomas | 2023/11/27 13:30 | Edoardo Lavagno v Ivan Gakhov | 5-7,6-7 |
| Challenger Valencia | 2023/11/21 11:50 | Ivan Gakhov v Andrea Pellegrino | 3-6,1-6 |
| Challenger Malaga | 2023/10/10 08:30 | Ivan Gakhov v Billy Harris | 3-6,4-6 |
| Challenger Lisbon | 2023/10/04 10:30 | Benjamin Hassan v Ivan Gakhov | 7-5,6-1 |
| Challenger Lisbon | 2023/10/03 13:30 | Geoffrey Blancaneaux v Ivan Gakhov | 4-6,2-6 |
| Challenger Braga | 2023/09/26 10:45 | Ivan Gakhov v Oriol Roca Batalla | 3-6,3-6 |
| Challenger Sibiu | 2023/09/22 09:15 | Ivan Gakhov v Nerman Fatic | 1-6,6-2,2-6 |
| Challenger Maspalomas | 2023/11/28 10:00 | Rudolf Molleker v Oleksii Krutykh | 6-4,4-6,2-6 |
| Challenger Valencia | 2023/11/22 10:00 | Alejandro Moro Canas v Rudolf Molleker | 6-4,6-4 |
| Challenger Valencia | 2023/11/20 16:35 | Rudolf Molleker v Alex Molcan | 6-4,7-5 |
| ITF M25 Antalya | 2023/11/15 11:30 | Rudolf Molleker v Marko Maksimovic | 6-7,2-6 |
| Challenger Ismaning | 2023/11/04 12:00 | Rudolf Molleker v Antoine Bellier | 6-7,2-6 |
| Challenger Ismaning | 2023/11/03 14:10 | Rudolf Molleker v Alibek Kachmazov | 7-5,6-7,6-3 |
| Challenger Ismaning | 2023/10/30 18:50 | Rudolf Molleker v Daniel Masur | 7-6,4-6,6-3 |
| Challenger Hamburg | 2023/10/17 11:30 | Rudolf Molleker v Akira Santillan | 3-6,4-6 |