| ITF - Rovinj M15 | 2023/03/12 12:00 | Maj Premzl v Benedikt Henning | 5-7,6-2,10-7 |
| ITF - Porec M15 | 2023/03/05 12:00 | Benedikt Henning v Maj Premzl | 2-6,6-7 |
| UTR Pro - Dubaj | 2023/02/12 05:00 | Mihai Razvan Marinescu v Benedikt Henning | 6-3,5-7,2-6 |
| UTR Pro - Dubaj | 2023/02/11 08:30 | Simon Roberts v Benedikt Henning | 6-7,5-7 |
| UTR Pro - Dubaj | 2023/02/10 06:30 | Kai Lemstra v Benedikt Henning | 7-5,6-1 |
| UTR Pro - Dubaj | 2023/02/09 05:00 | Luka Pavlovic v Benedikt Henning | 6-4,4-6,6-1 |
| UTR Pro - Dubaj | 2023/02/07 09:03 | Tomislav Jotovski v Benedikt Henning | 3-6,0-6 |
| UTR Pro - Dubaj | 2023/02/06 05:00 | Benedikt Henning v Lohithaksha Bathrinath | 6-2,1-6,6-4 |
| ITF - Opatija M15 | 2023/03/23 11:35 | Dusan Obradovic v Daniele Capecchi | 6-3,6-7,2-6 |
| ITF - Opatija M15 | 2023/03/22 14:15 | Marko Andrejic v Dusan Obradovic | 4-6,2-6 |
| ITF - Opatija M25 | 2023/03/21 09:30 | Dusan Obradovic v Federico Marchetti | 6-1,6-2 |
| ITF - Opatija M25 | 2023/03/20 14:30 | Dusan Obradovic v Lorenzo Vatteroni | 5-7,6-2,10-6 |
| ITF - Rovinj M15 | 2023/03/15 12:55 | Riccardo Balzerani v Dusan Obradovic | 6-3,7-5 |
| ITF - Rovinj M15 | 2023/03/14 11:00 | Dusan Obradovic v Artem Podorozhnyi | 6-0,6-2 |
| ITF - Rovinj M15 | 2023/03/13 10:30 | Dusan Obradovic v Simone Agostini | 7-6,7-6 |
| ITF - Rovinj M15 | 2023/03/12 12:00 | Dusan Obradovic v Niklas Waldner | 6-1,6-2 |