Stadium: Court 1 Round: 25 Ground: Clay
| 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 M15 - Pirot | 2023/09/07 07:30 | Francesco Ferrari v Dusan Obradovic | 1-6,2-6 |
| ITF M15 - Pirot | 2023/09/06 07:30 | Petr Bar Biryukov v Dusan Obradovic | 6-7,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/03 10:50 | Dusan Obradovic v Luka Pavlovic | 2-6,2-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/02 08:00 | Dusan Obradovic v Giannicola Misasi | 6-1,6-1 |
| ITF M15 - Kursumlijska Banja | 2023/09/01 10:00 | Emile Hudd v Dusan Obradovic | 4-6,5-7 |
| ITF M15 - Kursumlijska Banja | 2023/08/31 11:20 | Ioannis Kountourakis v Dusan Obradovic | 4-6,6-7 |
| ITF M15 - Pirot | 2023/09/05 12:55 | Filip Cristian Jianu v Milan Drinic | 4-6,6-4,6-4 |
| ITF M15 - Kursumlijska Banja | 2023/08/30 10:30 | Milan Drinic v Peter Fajta | 3-6,6-3,6-7 |
| ITF M25 - Osijek | 2023/08/10 09:45 | Milan Drinic v Sebastian Prechtel | 5-7,7-6,2-6 |
| 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 |