| ITF M15 - Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| ITF M15 - Pirot | 2023/09/05 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 - Kursumlijska Banja | 2023/09/18 07:00 | Obrad Markovski v Marko Nikolic | 1-6,7-5,8-10 |
| ITF M15 - Kursumlijska Banja | 2023/09/12 07:00 | Obrad Markovski v Sasa Markovic | 2-6,7-5,5-10 |
| ITF M15 - Kursumlijska Banja | 2023/09/11 07:00 | Obrad Markovski v Zekai Li | 2-6,6-2,10-4 |
| ITF M15 - Pirot | 2023/09/06 11:30 | Obrad Markovski v Viktor Jovic | 4-6,2-6 |
| ITF M15 - Pirot | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| ITF M15 - Pirot | 2023/09/04 07:30 | Obrad Markovski v Maxim Krapivin | 1-6,6-4,10-5 |
| ITF M15 - Kursumlijska Banja | 2023/08/30 13:35 | Obrad Markovski v Aleksa Pisaric | 4-6,5-7 |
| Davis Cup | 2023/06/17 09:00 | Marco De Rossi v Obrad Markovski | 6-0,6-1 |