| ITF - M15 Kuršumlijska Banja | 2023/06/21 10:15 | Milan Drinic v Sasa Markovic | 3-6,6-3,6-4 |
| 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 Kuršumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF - M15 Kuršumlijska 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 Kuršumlijska 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 |
| UTR Pro Beograd | 2023/10/07 11:06 | Sasa Markovic v Oleg Prihodko | 2-6,6-7 |
| 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 09:25 | Lazar Vojinovic v Sasa Markovic | 3-6,4-6 |
| UTR Pro Beograd | 2023/10/03 06:00 | Yuquan Jin v Sasa Markovic | 6-4,5-7,1-6 |
| UTR Pro Beograd | 2023/10/01 11:52 | Sasa Markovic v Aleksandar Mihailovic | 7-6,6-2 |
| ITF - M25 Zlatibor | 2023/09/28 13:35 | Jaka Protic Zakelj v Sasa Markovic | 6-4,3-6,12-10 |
| ITF - M15 Kuršumlijska Banja | 2023/09/14 08:00 | Sasa Markovic v Gabriele Pennaforti | 4-6,4-6 |
| ITF - M15 Kuršumlijska Banja | 2023/09/13 12:40 | Sasa Markovic v Aleksei Khomich | 6-1,3-6,6-3 |