Stadium: Court 6 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sharm El Sheikh | 2023/12/06 14:20 | Dusan Obradovic v Mees Rottgering | 0-6,3-6 |
| ITF M25 Pazardzhik | 2023/10/03 09:55 | Dusan Obradovic v Max Houkes | 1-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/20 11:35 | Gabriel Donev v Dusan Obradovic | 7-5,6-2 |
| ITF M15 Kursumlijska Banja | 2023/09/17 10:30 | Svyatoslav Gulin v Dusan Obradovic | 2-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/09/16 08:30 | Francesco Ferrari v Dusan Obradovic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/15 09:00 | Vlad Andrei Dancu v Dusan Obradovic | 6-3,3-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/09/14 10:20 | Dusan Obradovic v Nicolas Buitrago | 6-2,6-2 |
| ITF M15 Kursumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| ITF M15 Sharm El Sheikh | 2023/12/08 08:00 | Samuel Vincent Ruggeri v Max Wiskandt | 6-4,6-4 |
| ITF M15 Sharm El Sheikh | 2023/12/07 08:00 | Max Wiskandt v Boris Butulija | 7-6,6-2 |
| ITF M15 Sharm El Sheikh | 2023/12/06 14:30 | Jan Kupcic v Max Wiskandt | 3-6,0-6 |
| ITF M15 Monastir | 2023/11/15 11:10 | Christoph Negritu v Max Wiskandt | 6-3,6-2 |
| ITF M15 Monastir | 2023/11/12 09:00 | Egor Agafonov v Max Wiskandt | 6-4,4-6,7-6 |
| ITF M15 Monastir | 2023/11/11 09:00 | Max Wiskandt v Liam Gavrielides | 6-4,6-3 |
| ITF M15 Monastir | 2023/11/10 09:00 | Diego F Flores v Max Wiskandt | 7-5,5-7,3-6 |
| ITF M15 Monastir | 2023/11/09 08:30 | Max Wiskandt v Adriano Dzhenev | 6-0,6-3 |