| UTR Pro - Belgrado | 2023/04/14 07:00 | Milan Drinic v Kristian Juhas | 3-6,6-1,6-4 |
| UTR Pro - Belgrado | 2023/04/12 08:00 | Milan Drinic v Aleksa Pisaric | 6-4,2-6,6-3 |
| UTR Pro - Belgrado | 2023/04/11 09:00 | Milan Drinic v Petr Nesterov | 3-6,3-6 |
| ITF - M25 Opatija | 2023/03/19 08:00 | Milan Drinic v Maks Lukman | 6-7,6-2,10-12 |
| ITF - M15 Rovinj | 2023/03/16 09:00 | Federico Arnaboldi v Milan Drinic | 7-6,7-6 |
| ITF - M15 Rovinj | 2023/03/15 12:55 | Milan Drinic v Lucas Bouquet | 6-4,6-4 |
| ITF - M15 Rovinj | 2023/03/15 08:30 | Noah Perfetti v Milan Drinic | 1-6,3-6 |
| ITF - M15 Rovinj | 2023/03/13 10:30 | Andrea Bolla v Milan Drinic | 6-7,3-6 |
| UTR Pro - Belgrado | 2023/04/14 13:08 | Edison Ambarzumjan v Stefan Popovic | 1-6,1-5 |
| UTR Pro - Belgrado | 2023/04/13 10:00 | Maxime Hamou v Stefan Popovic | 6-1,5-1 |
| UTR Pro - Belgrado | 2023/04/11 09:00 | Adam Jurajda v Stefan Popovic | 6-7,7-6,7-6 |
| UTR Pro - Belgrado | 2023/04/10 10:23 | Stefan Popovic v Gorazd Srbljak | 5-7,6-3,6-1 |
| ITF - M15 Opatija | 2023/03/23 08:30 | Stefan Popovic v Remy Bertola | 5-7,6-3,5-7 |
| ITF - M15 Opatija | 2023/03/22 11:35 | Stefan Popovic v Matic Dimic | 6-3,6-2 |
| ITF - M15 Rovinj | 2023/03/14 11:55 | Stefan Popovic v Matej Dodig | 4-6,0-6 |
| ITF - M15 Antália | 2023/03/08 12:05 | Stefan Popovic v Maik Steiner | 6-4,1-6,6-7 |