Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Kursumlijska Banja | 2023/06/06 08:50 | Sergei Pogosian v Nikola Djosic | 6-1,6-3 |
| ITF M25 Kursumlijska Banja | 2023/06/05 08:30 | Nikola Djosic v S Mert Ozdemir | 6-3,6-4 |
| ITF M25 Kursumlijska Banja | 2023/06/04 12:30 | Danilo Ilic v Nikola Djosic | 0-6,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/17 16:15 | Nikola Djosic v Mwendwa Mbithi | 2-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/04/24 08:30 | Marko Stakusic v Nikola Djosic | 3-6,6-4,10-8 |
| ITF M15 Kursumlijska Banja | 2023/04/23 07:00 | Vanja Petrov v Nikola Djosic | 1-6,3-6 |
| ATP Belgrade | 2022/04/17 10:20 | Nikola Djosic v Flavio Cobolli | 1-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/08/29 09:45 | Ioannis Kountourakis v Maxim Krapivin | 6-2,6-4 |
| ITF M15 Kursumlijska Banja | 2023/08/28 12:00 | Lorenzo Vatteroni v Ioannis Kountourakis | 6-0,3-6,9-11 |
| ITF M15 Metzingen | 2023/07/23 07:30 | Ioannis Kountourakis v Stepan Mruzek | 3-6,5-7 |
| ITF M15 Sofia | 2023/07/03 09:30 | Ioannis Kountourakis v Adam Heinonen | 6-7,5-7 |
| ITF M15 Sofia | 2023/07/02 11:00 | Ioannis Kountourakis v Daniele Minighini | 6-3,6-3 |
| ITF M15 Belgrade | 2023/06/26 10:00 | Maxence Rivet v Ioannis Kountourakis | 6-3,6-2 |
| ITF M15 Belgrade | 2023/06/25 07:00 | Stefan Micov v Ioannis Kountourakis | 6-4,3-6,8-10 |
| ITF M15 Heraklion | 2023/03/19 07:00 | Ioannis Kountourakis v Mark Neyelov | 3-6,3-6 |