Stadium: COURT VIKTOR TROICKI Round: 26 Ground: Clay
| ITF M15 - Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/19 08:45 | Marko Nikolic v Ioannis Kountourakis | 4-6,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/18 11:00 | Aleksandar Mihailovic v Ioannis Kountourakis | 1-6,6-7 |
| ITF M15 - Kursumlijska Banja | 2023/09/13 11:35 | Vlad Andrei Dancu v Ioannis Kountourakis | 6-3,6-4 |
| ITF M15 - Kursumlijska Banja | 2023/09/12 07:00 | Antonio Massara v Ioannis Kountourakis | 6-7,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/11 09:30 | Ioannis Kountourakis v Pedro Iamachkine | 6-4,6-1 |
| ITF M15 - Kursumlijska Banja | 2023/09/10 07:00 | Ioannis Kountourakis v Jordi Garcia Mestre | 6-1,6-0 |
| ITF M15 - Pirot | 2023/09/05 10:05 | Obrad Markovski v Ioannis Kountourakis | 7-6,6-0 |
| ITF M15 - Kursumlijska Banja | 2023/09/20 08:35 | Tadija Radovanovic v Stefan Popovic | 4-6,2-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/15 07:55 | Stefan Popovic v Svyatoslav Gulin | 5-7,4-6 |
| ITF M15 - Kursumlijska Banja | 2023/09/14 11:40 | Stefan Popovic v Romeo Hadzimehmedovic | 6-2,6-3 |
| ITF M15 - Kursumlijska Banja | 2023/09/12 10:40 | Stefan Popovic v Jacques-Kai Inoue | 6-1,7-6 |
| ITF M25 - Maribor | 2023/09/06 09:30 | Bor Artnak v Stefan Popovic | 6-3,6-1 |
| ITF M25 - Maribor | 2023/08/31 14:25 | Stefan Popovic v Raphael Calzi | 7-6,6-2 |
| ITF M25 - Maribor | 2023/08/31 09:50 | Filip Cristian Jianu v Stefan Popovic | 5-7,4-6 |
| Challenger Banja Luka | 2023/08/07 16:00 | Miljan Zekic v Stefan Popovic | 6-3,6-0 |