Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| Challenger Blois | 2023/06/18 14:25 | Nikolas Sanchez Izquierdo v Jakub Paul | 7-6,3-6,6-1 |
| ITF M15 Duffel | 2023/06/13 16:05 | Jakub Paul v Marlon Vankan | 2-6,3-6 |
| ITF M15 Sarajevo | 2023/06/10 07:55 | Elmar Ejupovic v Jakub Paul | 6-7,6-4,6-4 |
| ITF M15 Sarajevo | 2023/06/09 09:45 | Jakub Paul v Petar Jovanovic | 6-2,6-2 |
| ITF M15 Sarajevo | 2023/06/08 06:55 | Jakub Paul v Nikola Basic | 6-1,6-0 |
| ITF M15 Sarajevo | 2023/06/06 12:35 | Jakub Paul v Matthias Ujvary | 6-3,7-5 |
| ITF M25 Most | 2023/05/26 08:00 | Michael Vrbensky v Jakub Paul | 6-2,6-3 |
| ITF M25 Most | 2023/05/25 10:30 | Jakub Paul v Hynek Barton | 4-6,7-5,7-5 |
| ITF M15 Kursumlijska Banja | 2023/05/05 07:30 | Adriano Dzhenev v Clement Tabur | 3-6,0-6 |
| ITF M15 Kursumlijska Banja | 2023/05/04 07:00 | Adriano Dzhenev v Samir Hamza Reguig | 6-4,6-3 |
| ITF M15 Kursumlijska Banja | 2023/05/02 13:05 | Hady Habib v Adriano Dzhenev | 6-7,1-6 |
| ITF M15 Antalya | 2023/04/06 07:30 | Adriano Dzhenev v Juan Pablo Paz | 3-6,6-7 |
| ITF M15 Antalya | 2023/04/05 07:25 | Adriano Dzhenev v Emir Sutekin | 5-7,6-1,6-2 |
| ITF M15 Antalya | 2023/03/29 07:30 | Juan Pablo Paz v Adriano Dzhenev | 6-4,6-3 |
| ITF M15 Sozopol | 2022/10/19 07:00 | Stefan Palosi v Adriano Dzhenev | 7-6,6-1 |
| ITF M15 Sozopol | 2022/10/11 09:30 | Alexandar Lazarov v Adriano Dzhenev | 6-4,6-4 |