| UTR Pro - Belgrad | 2023/10/12 07:30 | Milan Drinic v Domagoj Biljesko | 6-3,3-6,4-6 |
| UTR Pro - Belgrad | 2023/10/11 07:30 | Egor Gorin v Milan Drinic | 7-5,3-6,0-6 |
| UTR Pro - Belgrad | 2023/10/10 06:00 | Nini Gabriel Dica v Milan Drinic | 3-6,4-6 |
| UTR Pro - Belgrad | 2023/10/08 12:00 | Milan Drinic v Sasa Markovic | 4-6,2-6 |
| UTR Pro - Belgrad | 2023/10/04 06:00 | Vuk Radjenovic v Milan Drinic | 5-7,6-4,3-6 |
| UTR Pro - Belgrad | 2023/10/02 13:41 | Karlo Kajin v Milan Drinic | 3-6,6-0,6-2 |
| UTR Pro - Belgrad | 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 Davangere | 2023/10/25 05:00 | Dev Javia v Raghav Jaisinghani | 6-0,6-3 |
| ITF - M15 Davangere | 2023/10/23 03:45 | Raghav Jaisinghani v Jagmeet Singh | 6-3,6-3 |
| ITF - M15 Davangere | 2023/10/22 04:00 | Raghav Jaisinghani v Maanav Jain | 6-1,6-0 |
| ITF - M25 Dharwad | 2023/10/18 03:30 | Raghav Jaisinghani v Suraj R Prabodh | 4-6,4-6 |
| ITF - M15 Ahmedabad | 2023/10/12 05:30 | Raghav Jaisinghani v Sidharth Rawat | 3-6,5-7 |
| ITF - M15 Ahmedabad | 2023/10/11 05:45 | Rishab Agarwal v Raghav Jaisinghani | 7-5,2-6,6-7 |
| ITF - M15 Ahmedabad | 2023/10/10 07:30 | Raghav Jaisinghani v Adil Kalyanpur | 6-3,7-6 |
| ITF - M15 Ahmedabad | 2023/10/09 06:00 | Raghav Jaisinghani v Abhishek Bastola | 6-3,7-6 |