Stadium: Court 4 Round: 26 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/08/30 13:45 | Nikola Djosic v Ioannis Kountourakis | 4-6,7-6,1-6 |
| 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 Kursumlijska Banja | 2023/08/30 14:45 | Mihail Ivanov v Dusan Obradovic | 2-6,3-6 |
| ITF M25 Osijek | 2023/08/11 10:40 | Luka Mikrut v Dusan Obradovic | 7-6,6-3 |
| ITF M25 Osijek | 2023/08/10 13:10 | Dusan Obradovic v Luca Giacomini | 6-2,7-6 |
| ITF M25 Osijek | 2023/08/08 11:15 | Dusan Obradovic v Josip Simundza | 6-3,6-4 |
| ITF M15 Novi Sad | 2023/08/05 08:00 | Matej Dodig v Dusan Obradovic | 7-6,6-3 |
| ITF M15 Novi Sad | 2023/08/04 08:00 | Dusan Obradovic v Duje Kekez | 6-2,6-3 |
| ITF M15 Novi Sad | 2023/08/03 09:25 | Viktor Jovic v Dusan Obradovic | 0-6,6-3,2-6 |
| ITF M15 Novi Sad | 2023/08/02 12:10 | Vuk Radjenovic v Dusan Obradovic | 4-6,4-6 |