Stadium: Court 2 Round: 54 Ground: Clay
| ITF M15 Bad Waltersdorf | 2023/10/01 09:00 | Jan Kupcic v Artem Podorozhnyi | 4-6,6-2,10-5 |
| ITF M15 Arad | 2023/09/26 11:55 | Kai Wehnelt v Jan Kupcic | 3-6,7-6,6-4 |
| ITF M15 Arad | 2023/09/25 07:00 | Jan Kupcic v Samuil Konov | 7-6,4-6,10-6 |
| ITF M25 Maribor | 2023/09/06 09:50 | Jan Kupcic v Mathys Erhard | 6-4,1-6,4-6 |
| ITF M25 Maribor | 2023/08/31 08:50 | Jan Kupcic v Mirza Basic | 4-6,6-7 |
| ITF M15 Kottingbrunn | 2023/08/13 12:00 | Jan Kupcic v Dennis Dragomirov | 4-6,6-7 |
| ITF M25 Osijek | 2023/08/09 12:25 | Jan Kupcic v Luca Giacomini | 6-2,2-6,3-6 |
| ITF M15 Novi Sad | 2023/07/30 08:30 | Miha Vetrih v Jan Kupcic | 6-7,6-4,10-8 |
| ITF M15 Bad Waltersdorf | 2023/10/01 09:00 | Leon Benedict v Josip Simundza | 2-6,2-6 |
| ITF M25 Madrid | 2023/09/10 15:00 | Josip Simundza v Rodrigo Mora Clement | 6-2,6-4 |
| ITF M15 Budapest | 2023/09/06 10:00 | Josip Simundza v Gabriel Decamps | 1-6,4-6 |
| ITF M15 Budapest | 2023/09/04 10:00 | Josip Simundza v Kevin Humpfner | 2-6,3-6 |
| ITF M15 Budapest | 2023/09/03 09:30 | Josip Simundza v Gregor Hausberger | 6-1,5-7,12-10 |
| ITF M25 Osijek | 2023/08/08 11:15 | Dusan Obradovic v Josip Simundza | 6-3,6-4 |
| ITF M15 Celje | 2023/06/27 08:45 | Josip Simundza v Maurus Malgiaritta | 2-6,6-7 |
| ITF M15 Celje | 2023/06/26 09:30 | Michal Novansky v Josip Simundza | 2-6,4-6 |