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 |
| ATP Kitzbuhel | 2023/07/30 09:00 | Facundo Bagnis v Ivan Gakhov | 4-6,6-3,6-4 |
| ATP Kitzbuhel | 2023/07/29 09:00 | Kilian Feldbausch v Ivan Gakhov | 4-6,6-7 |
| ATP Hamburg | 2023/07/22 10:25 | Elias Ymer v Ivan Gakhov | 6-3,6-2 |
| ATP Gstaad | 2023/07/15 08:30 | Maximilian Neuchrist v Ivan Gakhov | 6-3,6-3 |
| Challenger Braunschweig | 2023/07/11 13:40 | Pierre-Hugues Herbert v Ivan Gakhov | 4-6,6-3,6-4 |
| Challenger Karlsruhe | 2023/07/07 14:00 | Giulio Zeppieri v Ivan Gakhov | 6-1,6-4 |
| Challenger Karlsruhe | 2023/07/06 09:00 | Rudolf Molleker v Ivan Gakhov | 4-6,6-3,3-6 |
| Challenger Karlsruhe | 2023/07/04 09:00 | Nerman Fatic v Ivan Gakhov | 6-7,2-6 |
| Challenger Meerbusch | 2023/08/09 09:55 | Ergi Kirkin v Rudolf Molleker | 6-4,7-6 |
| Challenger Luedenscheid | 2023/08/04 12:00 | Rudolf Molleker v Duje Ajdukovic | 2-6,4-6 |
| Challenger Luedenscheid | 2023/08/04 08:00 | Fabian Marozsan v Rudolf Molleker | 6-0,6-7,2-6 |
| Challenger Luedenscheid | 2023/08/01 15:15 | Max Hans Rehberg v Rudolf Molleker | 4-6,2-6 |
| ATP Hamburg | 2023/07/25 11:05 | Maximilian Marterer v Rudolf Molleker | 7-6,6-2 |
| Challenger Amersfoort | 2023/07/22 11:30 | Rudolf Molleker v Maximilian Marterer | 4-6,6-7 |
| Challenger Amersfoort | 2023/07/21 09:00 | Gauthier Onclin v Rudolf Molleker | 2-6,2-6 |
| Challenger Amersfoort | 2023/07/19 17:10 | Rudolf Molleker v Federico Delbonis | 6-1,6-3 |