Stadium: Court 6 Round: 62 Ground: Clay
| ITF M15 Kottingbrunn | 2023/08/13 12:00 | Jan Kupcic v Dennis Dragomirov | 4-6,6-7 |
| 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 Kottingbrunn | 2023/08/14 08:00 | Andrej Krajcik v Gal Emersic Potocnik | 6-2,6-1 |
| ITF M15 Novi Sad | 2023/07/23 13:00 | Aleksandar Mihailovic v Andrej Krajcik | 6-0,0-6,10-7 |
| ITF M25 Telfs | 2023/07/16 09:00 | Edoardo Cherie Ligniere v Andrej Krajcik | 4-6,6-3,10-5 |
| ITF M25 Poprad | 2023/06/19 10:30 | Ivan Denisov v Andrej Krajcik | 7-5,6-3 |
| ITF M25 Poprad | 2023/06/18 08:00 | Samuel Paulovcak v Andrej Krajcik | 6-7,4-6 |
| ITF M15 Sarajevo | 2023/06/06 07:25 | Andrej Krajcik v Bozo Barun | 2-6,2-6 |
| ITF M25 Kiseljak | 2023/05/30 10:05 | Marko Stakusic v Andrej Krajcik | 2-6,6-2,10-6 |
| ITF M25 Kiseljak | 2023/05/29 09:30 | Andrej Krajcik v Sasa Markovic | 6-4,1-6,10-8 |