| 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 M25 Kursumlijska Banja | 2023/05/19 10:10 | Milan Drinic v Mikalai Haliak | 3-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/18 15:30 | Miljan Zekic v Milan Drinic | 3-6,6-3,6-7 |
| ITF M25 Kursumlijska Banja | 2023/05/17 07:00 | Milan Drinic v Timofey Stepanov | 3-6,6-3,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/16 06:55 | Milan Drinic v Nikola Mitrovic | 6-1,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/30 09:05 | Geni Inoue v Obrad Markovski | 4-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/05/29 11:30 | Federico Hernan Giovanniello v Obrad Markovski | 4-6,2-6 |
| Challenger Skopje | 2023/05/22 09:00 | Karol Drzewiecki v Obrad Markovski | 6-2,7-5 |
| Challenger Skopje | 2023/05/21 10:15 | Obrad Markovski v Evgeny Karlovskiy | 6-2,6-1 |
| ITF M15 Osijek | 2023/05/02 09:45 | Obrad Markovski v Michael Gloeckler | 5-7,2-6 |
| ITF M15 Osijek | 2023/05/01 13:00 | Obrad Markovski v Jiri Krouzek | 7-5,6-4 |
| UTR Pro Beograd | 2023/04/22 09:51 | Maxime Hamou v Obrad Markovski | 3-6,7-5,6-3 |
| UTR Pro Beograd | 2023/04/21 06:00 | Aleksei Khomich v Obrad Markovski | 3-6,0-0 |