Stadium: Court 1 Round: 19 Ground: Clay
| Challenger Augsburg | 2023/08/20 09:30 | Sandro Kopp v Hendrik Jebens | 6-7,2-6 |
| Challenger Braunschweig | 2023/07/10 09:00 | Daniel Masur v Hendrik Jebens | 6-3,3-6,6-3 |
| Challenger Braunschweig | 2023/07/09 13:00 | Hendrik Jebens v Ramkumar Ramanathan | 6-1,6-4 |
| Challenger Heilbronn | 2023/06/04 09:30 | Hendrik Jebens v Max Hans Rehberg | 6-7,6-7 |
| Challenger Mauthausen | 2023/05/09 09:25 | Marius Copil v Hendrik Jebens | 6-7,6-3,6-4 |
| Challenger Mauthausen | 2023/05/08 08:00 | Benjamin Hassan v Hendrik Jebens | 2-6,6-7 |
| Challenger Mauthausen | 2023/05/07 08:00 | Hendrik Jebens v Jerome Kym | 6-4,6-4 |
| Challenger Rennes | 2022/09/12 14:05 | Karl Friberg v Hendrik Jebens | 6-4,6-4 |
| Challenger Augsburg | 2023/08/20 08:00 | Sebastian Prechtel v Gianmarco Ferrari | 3-6,3-6 |
| Challenger Cordenons | 2023/08/07 16:15 | Gianmarco Ferrari v Lukas Neumayer | 4-6,2-6 |
| Challenger San Marino | 2023/07/31 09:00 | Kyrian Jacquet v Gianmarco Ferrari | 6-4,6-4 |
| Challenger San Marino | 2023/07/30 08:00 | Simone Roncalli v Gianmarco Ferrari | 5-7,6-3,0-6 |
| Challenger Zug | 2023/07/25 08:50 | Arthur Rinderknech v Gianmarco Ferrari | 7-6,6-3 |
| Challenger Zug | 2023/07/24 12:10 | Gianmarco Ferrari v Vladyslav Orlov | 6-3,6-4 |
| Challenger Zug | 2023/07/23 13:20 | Joao Lucas Reis da Silva v Gianmarco Ferrari | 3-6,6-7 |
| Challenger San Benedetto | 2023/07/11 12:55 | Gianmarco Ferrari v Flavio Cobolli | 3-6,1-6 |