Stadium: Court 22 Round: 25 Ground: Clay
| ITF M15 - Antalya | 2023/02/21 07:00 | Denis Klok v Dominik Kellovsky | 6-2,6-3 |
| ITF M15 - Antalya | 2023/02/20 12:15 | Denis Klok v Haydar C Gokpinar | 7-6,6-3 |
| ITF M25 Antalya | 2023/02/05 07:00 | Denis Klok v Stephanos Schinas | 6-3,6-3 |
| ITF M25 Antalya | 2023/02/01 10:35 | Denis Klok v Valerio Aboian | 4-6,6-3,1-6 |
| ITF M25 Antalya | 2023/01/31 07:10 | Denis Klok v Stephanos Schinas | 6-2,6-1 |
| ITF M25 Antalya | 2023/01/30 12:30 | Denis Klok v Utku Kerem Biberli | 6-1,6-1 |
| ITF M25 Dauhá | 2023/01/17 13:30 | Marius Copil v Denis Klok | 6-2,6-7,6-2 |
| ITF M25 Dauhá | 2023/01/16 12:00 | Denis Klok v Guy Den Heijer | 6-2,3-6,10-5 |
| ITF M15 Sozopol | 2022/10/11 07:00 | Iliyan Radulov v Alexander Donski | 6-4,6-7,4-6 |
| ITF M15 Sozopol | 2022/10/06 09:10 | Iliyan Radulov v Olaf Pieczkowski | 2-6,2-6 |
| ITF M15 Sozopol | 2022/10/05 07:00 | Simeon Terziev v Iliyan Radulov | 4-6,3-6 |
| ITF M15 Sofie | 2022/07/05 08:40 | Iliyan Radulov v Rrezart Cungu | 4-6,6-4,3-6 |
| UTR Pro Tennis Series - Pazardžik | 2021/07/17 12:00 | Iliyan Radulov v Plamen Milushev | 6-3,1-6,2-6 |
| UTR Pro Tennis Series - Pazardžik | 2021/07/16 07:30 | Iliyan Radulov v Ilya Snitari | 3-6,2-6 |
| UTR Pro Tennis Series - Pazardžik | 2021/07/15 10:30 | Iliyan Radulov v Denislav Prodanov | 2-6,2-6 |
| UTR Pro Tennis Series - Pazardžik | 2021/07/14 06:00 | Dian Nedev v Iliyan Radulov | 7-5,6-1 |