Stadium: Court 1 Round: 25 Ground: Clay
| 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 Novi Sad | 2023/07/25 07:30 | Tom Paris v Jan Kupcic | 6-2,6-3 |
| ITF - M15 Novi Sad | 2023/07/24 07:30 | Marcell Bartakovics v Jan Kupcic | 4-6,4-6 |
| ITF - M15 Novi Sad | 2023/07/23 07:00 | Niccolo Ciavarella v Jan Kupcic | 3-6,3-6 |
| ITF - M15 Celje | 2023/06/29 07:30 | Jan Kupcic v Sebastian Sorger | 5-7,6-7 |
| Challenger - Praga | 2023/08/23 08:00 | Andrew Paulson v Mathys Erhard | 6-3,6-3 |
| Challenger - Praga | 2023/08/22 08:00 | Mathys Erhard v Francesco Maestrelli | 7-6,5-7,6-3 |
| Challenger - Todi | 2023/08/16 12:00 | Gabriel Debru v Mathys Erhard | 6-4,2-6,6-4 |
| Challenger - Todi | 2023/08/15 16:35 | Lorenzo Giustino v Mathys Erhard | 6-7,0-6 |
| Challenger - Todi | 2023/08/14 11:45 | Mathys Erhard v Felix Gill | 6-1,3-6,0-6 |
| Challenger - Todi | 2023/08/13 15:00 | Mathys Erhard v Ramkumar Ramanathan | 6-4,6-2 |
| ITF - M25 Bolzano | 2023/08/05 08:55 | Mathys Erhard v Giovanni Oradini | 6-4,3-6,6-7 |
| ITF - M25 Bolzano | 2023/08/04 10:35 | Mathys Erhard v Gian M Di Natale | 6-2,6-4 |