Stadium: Hrastnik 4 Round: 54 Ground: Clay
| ITF M15 Kottingbrunn | 2023/08/13 12:00 | Jan Kupcic v Dennis Dragomirov | 4-6,6-7 |
| ITF M15 Bad Waltersdorf | 2022/08/15 07:00 | Jan Kupcic v Dennis Dragomirov | 3-6,4-6 |
| ITF M15 Vrhnika | 2024/05/29 16:15 | Jan Kupcic v Alessandro Pecci | 7-6,6-7,1-6 |
| ITF M15 Celje | 2024/05/20 14:05 | Jan Kupcic v Jiri Barnat | 4-6,2-6 |
| ITF M15 Doboj | 2024/05/09 11:25 | Jan Kupcic v Andrej Nedic | 1-6,6-4,6-7 |
| ITF M15 Doboj | 2024/05/08 07:30 | Michael Gloeckler v Jan Kupcic | 3-6,6-3,0-6 |
| ITF M15 Doboj | 2024/05/07 08:55 | Jan Kupcic v Tilen Kovac | 6-1,6-0 |
| ITF M15 Doboj | 2024/05/06 10:00 | Jan Kupcic v Vladan Tadic | 6-1,6-4 |
| ITF M15 Osijek | 2024/05/01 11:05 | Jan Kupcic v Dusan Obradovic | 3-6,2-6 |
| ITF M15 Osijek | 2024/04/30 11:20 | Jan Kupcic v Domagoj Biljesko | 6-4,6-2 |
| ITF M15 Osijek | 2024/04/28 07:00 | Matias Riva v Dennis Dragomirov | 7-6,6-4 |
| ITF M15 Split | 2024/04/22 08:00 | Dennis Dragomirov v Karol Filar | 3-6,4-6 |
| ITF M15 Dubrovnik | 2024/04/14 10:15 | Dennis Dragomirov v Maks Meh | 6-7,1-6 |
| ITF M25 Trimbach | 2024/03/11 12:15 | Tanguy Genier v Dennis Dragomirov | 6-3,6-2 |
| ITF M15 Oberhaching | 2024/02/11 11:25 | Jannik Opitz v Dennis Dragomirov | 6-4,6-4 |
| ITF M25 Heraklion | 2023/11/28 09:30 | Evgenios Vasilakis v Dennis Dragomirov | 6-2,3-6,14-12 |
| ITF M25 Heraklion | 2023/11/27 08:00 | Brett Winters v Dennis Dragomirov | 5-7,1-6 |
| ITF M15 Heraklion | 2023/11/20 10:00 | Dennis Dragomirov v Vasil Yehorov | 6-3,3-6,9-11 |