Stadium: Court 4 Round: 25 Ground: Clay
| 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 Pirot | 2023/09/09 10:30 | Filip Cristian Jianu v Dusan Obradovic | 6-3,6-1 |
| ITF M15 Pirot | 2023/09/08 09:50 | Antonio Massara v Dusan Obradovic | 2-6,2-6 |
| ITF M25 Pazardzhik | 2023/09/30 07:00 | Max Houkes v Clement Tabur | 4-6,5-7 |
| ITF M25 Pazardzhik | 2023/09/29 07:00 | Hynek Barton v Max Houkes | 3-6,2-6 |
| ITF M25 Pazardzhik | 2023/09/28 07:00 | Simone Agostini v Max Houkes | 2-6,4-6 |
| ITF M25 Pazardzhik | 2023/09/27 07:00 | Filip Duda v Max Houkes | 2-6,6-7 |
| ITF M15 Haren | 2023/09/07 17:30 | Max Houkes v Stijn Pel | 4-6,6-3,2-6 |
| ITF M15 Haren | 2023/09/06 10:50 | Max Houkes v Alen Moritz Hodzic | 6-4,6-4 |
| ITF M25 Oldenzaal | 2023/09/02 13:50 | Lucas Gerch v Max Houkes | 6-3,6-4 |
| ITF M25 Oldenzaal | 2023/09/01 16:00 | Jeremy Jahn v Max Houkes | 3-6,6-7 |