Stadium: Center Court Round: 26 Ground: Clay
| Challenger Augsburg | 2023/08/21 12:00 | Santiago Rodriguez Taverna v Louis Wessels | 5-7,6-7 |
| Challenger Meerbusch | 2023/08/10 12:15 | Louis Wessels v Jan Choinski | 2-6,7-6,6-7 |
| Challenger Meerbusch | 2023/08/09 08:00 | Miguel Damas v Louis Wessels | 4-6,2-6 |
| Challenger Luedenscheid | 2023/08/04 09:50 | Louis Wessels v Pedro Martinez | 4-6,2-6 |
| Challenger Luedenscheid | 2023/08/02 12:45 | Louis Wessels v Marcelo Zormann | 6-3,7-6 |
| Challenger Pozoblanco | 2023/07/17 21:30 | Mattia Bellucci v Louis Wessels | 7-6,6-3 |
| ITF M25 Kassel | 2023/07/12 15:50 | Louis Wessels v Buvaysar Gadamauri | 6-7,6-2,3-6 |
| ITF M25 Marburg | 2023/07/09 10:55 | Timo Stodder v Louis Wessels | 6-4,6-3 |
| Challenger Augsburg | 2023/08/22 09:20 | Gianmarco Ferrari v Billy Harris | 6-7,6-1,6-4 |
| Challenger Augsburg | 2023/08/21 08:00 | Hendrik Jebens v Gianmarco Ferrari | 6-7,3-6 |
| 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 |