Stadium: Court 1 Round: 26 Ground: Clay
| ITF M25 Osijek | 2023/08/08 10:55 | Viktor Jovic v Milan Drinic | 2-6,3-6 |
| ITF M15 Novi Sad | 2023/08/01 11:10 | Kristijan Juhas v Milan Drinic | 6-3,1-6,13-11 |
| ITF M15 Novi Sad | 2023/07/31 15:40 | Nini Gabriel Dica v Milan Drinic | 3-6,6-7 |
| ITF M15 Novi Sad | 2023/07/30 08:30 | Aleksandar Mihailovic v Milan Drinic | 5-7,1-6 |
| ITF M15 Novi Sad | 2023/07/24 13:10 | Milan Drinic v Shendrit Deari | 6-4,5-7,4-10 |
| ITF M15 Belgrade | 2023/06/25 07:00 | Milan Drinic v Irakli Tsurtsumia | 6-0,3-6,14-16 |
| ITF M15 Kursumlijska Banja | 2023/06/22 10:05 | Andrey Chepelev v Milan Drinic | 6-3,6-3 |
| ITF M15 Kursumlijska Banja | 2023/06/21 10:15 | Milan Drinic v Sasa Markovic | 3-6,6-3,6-4 |
| ITF M25 Osijek | 2023/08/09 09:20 | Gorazd Srbljak v Sebastian Prechtel | 3-6,7-5,3-6 |
| ITF M25 Kramsach | 2023/07/27 10:30 | Lukas Rosol v Sebastian Prechtel | 6-2,6-4 |
| ITF M25 Kramsach | 2023/07/26 10:00 | Sebastian Prechtel v Milos Karol | 7-5,7-6 |
| ITF M15 Uslar | 2023/07/23 12:00 | Sebastian Prechtel v Stefan Popovic | 6-3,4-6,6-3 |
| ITF M15 Uslar | 2023/07/22 09:45 | Christoph Negritu v Sebastian Prechtel | 2-6,4-6 |
| ITF M15 Uslar | 2023/07/21 11:25 | Sebastian Prechtel v John Sperle | 6-3,6-1 |
| ITF M15 Uslar | 2023/07/20 10:25 | Sebastian Prechtel v Jakub Nicod | 6-2,6-2 |
| ITF M15 Uslar | 2023/07/18 10:00 | Sebastian Prechtel v Svyatoslav Gulin | 6-1,6-3 |