Stadium: Court 1 Round: 62 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/06/18 07:00 | Milan Drinic v Novak Novakovic | 6-3,6-7,13-11 |
| ITF M15 Kursumlijska Banja | 2023/06/02 10:30 | Alvaro Guillen Meza v Milan Drinic | 6-2,3-6,7-6 |
| ITF M15 Kursumlijska Banja | 2023/06/01 07:30 | Nikita Mashtakov v Milan Drinic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/05/31 07:00 | Milan Drinic v Tomas Farjat | 6-4,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/30 10:20 | Milan Drinic v Nicolas Villalon | 4-6,6-1,2-10 |
| ITF M15 Kursumlijska Banja | 2023/05/28 14:00 | Bautista Vilicich v Milan Drinic | 5-7,6-4,8-10 |
| ITF M15 Brcko | 2023/05/23 07:30 | Igor Gimenez v Milan Drinic | 7-6,6-4 |
| ITF M15 Brcko | 2023/05/22 13:00 | Vitali Shvets v Milan Drinic | 1-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/06/18 11:00 | Jan Kobierski v Relja Eskic | 6-2,7-6 |
| ITF M25 Kursumlijska Banja | 2023/06/05 13:50 | Sergei Pogosian v Jan Kobierski | 7-5,6-2 |
| ITF M25 Kursumlijska Banja | 2023/06/04 13:00 | Nikola Mitrovic v Jan Kobierski | 6-4,1-6,8-10 |
| ITF M15 Kursumlijska Banja | 2023/05/30 07:00 | Jan Kobierski v Erik Arutiunian | 0-6,6-1,10-12 |
| ITF M15 Kursumlijska Banja | 2023/05/29 09:05 | Mwendwa Mbithi v Jan Kobierski | 5-7,4-6 |
| ITF M15 Kursumlijska Banja | 2023/05/28 07:00 | Luka Petrovic v Jan Kobierski | 6-1,3-6,6-10 |
| ITF M15 Monastir | 2023/04/30 11:30 | Oskari Eerola v Jan Kobierski | 1-6,3-6 |
| ITF M15 Antalya | 2023/04/09 06:30 | Jan Kobierski v Seydina Andre | 1-6,1-6 |