| UTR Pro - Dubai | 2023/11/20 05:00 | Milan Drinic v Lun Obrul | 6-2,6-1 |
| UTR Pro - Dubai | 2023/11/18 11:38 | Charles Bertimon v Milan Drinic | 7-6,6-2 |
| UTR Pro - Dubai | 2023/11/17 11:48 | Dmitri Vlasov v Milan Drinic | 7-6,5-7,1-4 |
| UTR Pro - Dubai | 2023/11/16 05:00 | Giuseppe Tresca v Milan Drinic | 7-6,6-4 |
| UTR Pro - Dubai | 2023/11/14 05:00 | Dragos Constantin Ignat v Milan Drinic | 4-6,7-5,5-7 |
| UTR Pro - Dubai | 2023/11/13 08:07 | Milan Drinic v Raghav Jaisinghani | 6-3,5-3 |
| UTR Pro - Belgrad | 2023/10/12 07:30 | Milan Drinic v Domagoj Biljesko | 6-3,3-6,4-6 |
| UTR Pro - Belgrad | 2023/10/11 07:30 | Egor Gorin v Milan Drinic | 7-5,3-6,0-6 |
| UTR Pro - Dubai | 2023/11/20 05:00 | Benedikt Henning v Lazar Vojinovic | 6-7,7-6,6-3 |
| UTR Pro - Dubai | 2023/11/18 08:32 | Dmitri Vlasov v Benedikt Henning | 6-2,7-6 |
| UTR Pro - Dubai | 2023/11/17 07:30 | Benedikt Henning v Gabriel Donev | 6-4,7-5 |
| UTR Pro - Dubai | 2023/11/15 05:00 | Benedikt Henning v Lazar Vojinovic | 6-4,6-3 |
| UTR Pro - Dubai | 2023/11/13 06:30 | Koray Kirci v Benedikt Henning | 3-6,7-5,0-6 |
| 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 |