Stadium: Center Court Round: 19 Ground: Carpet indoor
| 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 |
| ITF M25 Zlatibor | 2023/09/29 13:30 | Matej Dodig v Andrew Paulson | 4-6,2-6 |
| Challenger Ismaning | 2023/10/29 15:50 | Tom Gentzsch v Elmar Ejupovic | 7-6,7-6 |
| ITF M15 Monastir | 2023/10/20 08:30 | Mohamed Aziz Dougaz v Tom Gentzsch | 6-1,6-4 |
| ITF M15 Monastir | 2023/10/19 08:00 | Samir Hamza Reguig v Tom Gentzsch | 2-6,4-6 |
| ITF M15 Monastir | 2023/10/17 10:05 | Yuta Kikuchi v Tom Gentzsch | 2-6,6-7 |
| ITF M15 Monastir | 2023/10/14 09:50 | Maxence Beauge v Tom Gentzsch | 7-6,6-2 |
| ITF M15 Monastir | 2023/10/13 08:00 | Adrien Gobat v Tom Gentzsch | 2-6,4-6 |
| ITF M15 Monastir | 2023/10/12 08:00 | Aziz Ouakaa v Tom Gentzsch | 6-7,6-2,5-7 |
| ITF M15 Monastir | 2023/10/10 08:00 | Josh Roe Flannelly v Tom Gentzsch | 4-6,0-6 |