Stadium: Center Court Round: 25 Ground: Carpet indoor
| Challenger Ismaning | 2023/10/30 14:15 | Andrew Paulson v Tom Gentzsch | 3-6,7-6,7-6 |
| Challenger Ismaning | 2023/10/29 15:50 | Andrew Paulson v Jakob Schnaitter | 6-3,7-5 |
| Challenger Ortisei | 2023/10/24 10:25 | Andrew Paulson v Lukas Klein | 5-7,4-6 |
| Challenger Hamburg | 2023/10/15 13:10 | Andrew Paulson v Daniel Masur | 3-6,2-6 |
| Challenger Bratislava | 2023/10/11 12:40 | Andrew Paulson v Luca Nardi | 7-5,4-6,3-6 |
| Challenger Bratislava | 2023/10/10 09:00 | Andrew Paulson v Gabi Adrian Boitan | 6-4,6-3 |
| ITF M25 Zlatibor | 2023/10/01 09:55 | Valentin Vacherot v Andrew Paulson | 3-6,7-5,3-6 |
| ITF M25 Zlatibor | 2023/09/30 08:30 | Andrew Paulson v Sebastian Gima | 6-4,6-1 |
| Challenger Ismaning | 2023/10/30 14:00 | Marius Copil v Louis Wessels | 6-3,4-6,3-6 |
| Challenger Ismaning | 2023/10/29 17:20 | Hazem Naw v Louis Wessels | 6-4,6-7,5-7 |
| Challenger Ortisei | 2023/10/25 08:00 | Luca Giacomini v Louis Wessels | 6-3,6-4 |
| Challenger Hamburg | 2023/10/15 11:45 | Louis Wessels v Akira Santillan | 1-6,2-6 |
| ITF M25 Sabadell | 2023/09/27 12:05 | Louis Wessels v Felix Gill | 0-6,3-6 |
| ITF M25 Pardubice | 2023/09/24 07:55 | Jonas Forejtek v Louis Wessels | 4-6,6-4,3-6 |
| ITF M25 Pardubice | 2023/09/23 11:25 | Louis Wessels v Martin Krumich | 6-1,6-4 |
| ITF M25 Pardubice | 2023/09/22 10:35 | Matej Dodig v Louis Wessels | 7-6,3-6,2-6 |