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 Sharm El Sheikh | 2023/12/13 09:35 | Michael Bassem Sobhy v Jan Kupcic | 2-6,6-4,7-6 |
| ITF M15 Sharm El Sheikh | 2023/12/12 09:10 | Jan Kupcic v Thomas Gerbaud | 5-7,7-6,10-4 |
| ITF M15 Sharm El Sheikh | 2023/12/11 10:00 | Jan Kupcic v Akram El Sallaly | 4-6,6-2,10-7 |
| ITF M15 Sharm El Sheikh | 2023/12/06 14:30 | Jan Kupcic v Max Wiskandt | 3-6,0-6 |
| ITF M15 Sharm El Sheikh | 2023/12/05 09:55 | Jan Kupcic v Stepan Pecak | 6-2,6-4 |
| ITF M15 Sharm El Sheikh | 2023/12/03 10:30 | Jan Kupcic v David Kim | 6-3,6-1 |
| ITF M15 Sharm El Sheikh | 2023/11/30 08:00 | Evgeny Philippov v Jan Kupcic | 6-3,2-6,6-3 |
| ITF M15 Sharm El Sheikh | 2023/11/29 09:05 | Tomas Lanik v Jan Kupcic | 4-6,3-6 |
| 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 |
| ITF M15 Heraklion | 2023/11/19 07:00 | Tomas Krcma v Dennis Dragomirov | 2-6,0-6 |
| UTR Pro Olomouc | 2023/11/12 07:00 | Dennis Dragomirov v Jiri Cizek | 6-3,6-4 |
| UTR Pro Olomouc | 2023/11/11 07:00 | Domagoj Biljesko v Dennis Dragomirov | 3-6,6-7 |
| UTR Pro Olomouc | 2023/11/10 09:48 | Dennis Dragomirov v Oleg Prihodko | 2-6,3-6 |
| UTR Pro Olomouc | 2023/11/09 10:00 | Dennis Dragomirov v Jakub Vrba | 6-3,7-5 |