| ITF Serbia F5 | 2017/09/07 07:00 | Milan Drinic v Domagoj Biljesko | 0-6,1-6 |
| ITF Greece F10 | 2016/11/15 10:45 | Milan Drinic v Domagoj Biljesko | 3-6,7-6,6-0 |
| UTR Pro Beograd | 2023/10/11 07:30 | Egor Gorin v Milan Drinic | 7-5,3-6,0-6 |
| UTR Pro Beograd | 2023/10/10 06:00 | Nini Gabriel Dica v Milan Drinic | 3-6,4-6 |
| UTR Pro Beograd | 2023/10/08 12:00 | Milan Drinic v Sasa Markovic | 4-6,2-6 |
| UTR Pro Beograd | 2023/10/04 06:00 | Vuk Radjenovic v Milan Drinic | 5-7,6-4,3-6 |
| UTR Pro Beograd | 2023/10/02 13:41 | Karlo Kajin v Milan Drinic | 3-6,6-0,6-2 |
| UTR Pro Beograd | 2023/10/01 09:43 | Milan Drinic v Obrad Markovski | 2-6,5-7 |
| 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 |
| UTR Pro Beograd | 2023/10/11 07:30 | Tadija Radovanovic v Domagoj Biljesko | 0-6,1-5 |
| UTR Pro Beograd | 2023/10/10 06:00 | Stefan Popovic v Domagoj Biljesko | 6-0,6-4 |
| UTR Pro Beograd | 2023/10/08 09:00 | Christos Keisidis v Domagoj Biljesko | 4-6,0-6 |
| UTR Pro Beograd | 2023/10/06 11:22 | Domagoj Biljesko v Sasa Markovic | 6-7,7-5,3-6 |
| UTR Pro Beograd | 2023/10/04 12:03 | Domagoj Biljesko v Zekai Li | 6-0,5-2 |
| UTR Pro Beograd | 2023/10/03 09:33 | Domagoj Biljesko v Aleksa Mardjonovic | 6-0,4-6,6-2 |
| UTR Pro Beograd | 2023/10/02 06:00 | Domagoj Biljesko v Enrique Bogo | 6-1,6-7,5-1 |
| ITF M25 Zlatibor | 2023/09/27 09:00 | Niksa Arsic v Domagoj Biljesko | 6-4,6-4 |