Stadium: Court 3 Round: 62 Ground: Clay
| ITF M15 Bad Waltersdorf | 2022/08/15 07:00 | Jan Kupcic v Dennis Dragomirov | 3-6,4-6 |
| 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 |
| ITF M15 Celje | 2023/06/28 13:05 | Maurus Malgiaritta v Jan Kupcic | 6-7,4-6 |
| ITF M15 Store | 2023/06/19 07:55 | Ivan Kremenchutskyi v Jan Kupcic | 6-4,6-3 |
| ITF M15 Frankfurt Am Main | 2023/08/07 08:00 | John H Lithen v Dennis Dragomirov | 6-2,6-4 |
| ITF M15 Novi Sad | 2023/07/31 07:00 | Nikola Mitrovic v Dennis Dragomirov | 6-4,4-6,11-9 |
| ITF M25 Telfs | 2023/07/17 13:45 | Timofey Stepanov v Dennis Dragomirov | 6-4,6-4 |
| ITF M25 Telfs | 2023/07/17 07:00 | Dennis Dragomirov v Davide Ferrarolli | 6-4,6-3 |
| ITF M25 Telfs | 2023/07/16 10:30 | Dennis Dragomirov v Francesco Schmitz | 6-1,6-2 |
| ITF M15 Sofia | 2023/07/05 09:30 | Dennis Dragomirov v Andreja Petrovic | 0-6,4-6 |
| ITF M15 Store | 2023/06/21 15:00 | Dennis Dragomirov v Dominik Kellovsky | 1-6,2-6 |
| ITF M15 Store | 2023/06/20 07:55 | Maurus Malgiaritta v Dennis Dragomirov | 2-6,6-3,7-10 |