Stadium: Court 7 Round: 62 Ground: Clay
| ITF M15 - Kottingbrunn | 2023/08/15 07:55 | Mohamed Safwat v Dennis Dragomirov | 6-4,6-4 |
| ITF M15 - Kottingbrunn | 2023/08/14 10:30 | Dennis Dragomirov v Andrej Krajcik | 6-4,6-2 |
| 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 |