Ground: Hardcourt outdoor
| ITF M15 Szczawno | 2023/08/30 10:05 | Patrick Zahraj v Benedikt Henning | 3-6,6-1,6-1 |
| ITF M15 Trier | 2023/08/24 12:40 | Jannik Maute v Benedikt Henning | 6-1,7-5 |
| ITF M15 Trier | 2023/08/23 10:30 | Kevin Humpfner v Benedikt Henning | 1-6,4-6 |
| ITF M15 Uberlingen | 2023/08/15 14:55 | Benedikt Henning v Marvin Schaber | 2-6,5-7 |
| ITF M25 Kassel | 2023/07/10 14:00 | Benedikt Henning v Martin Benes | 6-7,7-5,12-14 |
| ITF M25 Brasov | 2023/07/03 10:20 | Mihai Razvan Marinescu v Benedikt Henning | 6-3,6-2 |
| ITF M15 Kamen | 2023/06/26 08:00 | Benedikt Henning v Lambert Ruland | 4-6,3-6 |
| ITF M15 Kamen | 2023/06/26 08:00 | Benedikt Henning v Hans Albert Schubert | 6-4,4-6,10-7 |
| UTR Pro Beograd | 2023/10/14 08:33 | Andrej Nedic v Stefan Popovic | 7-5,6-1 |
| UTR Pro Beograd | 2023/10/13 09:06 | Stefan Popovic v Illya Beloborodko | 6-2,6-4 |
| UTR Pro Beograd | 2023/10/11 07:30 | Stefan Popovic v Christos Keisidis | 6-3,6-2 |
| UTR Pro Beograd | 2023/10/10 06:00 | Stefan Popovic v Domagoj Biljesko | 6-0,6-4 |
| UTR Pro Beograd | 2023/10/09 12:08 | Stefan Popovic v Tadija Radovanovic | 6-3,7-5 |
| UTR Pro Beograd | 2023/10/05 10:02 | Ilya Snitari v Stefan Popovic | 7-6,6-4 |
| UTR Pro Beograd | 2023/10/04 13:56 | Stefan Popovic v Egor Khotchenkov | 6-1,6-0 |
| UTR Pro Beograd | 2023/10/03 08:20 | Stefan Popovic v Strahinja Rakic | 6-3,6-0 |