Stadium: Court 3 Round: 28 Ground: Clay
| ITF - Antalya M15 | 2023/02/22 07:00 | Denis Klok v Iliyan Radulov | 6-3,6-0 |
| ITF - Pazardzhik M15 | 2023/05/20 07:00 | Gabriel Donev v Denis Klok | 6-7,5-7 |
| ITF - Pazardzhik M15 | 2023/05/19 09:45 | Alexander Vasilev v Denis Klok | 2-6,3-6 |
| ITF - Pazardzhik M15 | 2023/05/18 09:00 | Vlad Stoica v Denis Klok | 0-6,3-6 |
| ITF - Doboj M15 | 2023/05/12 07:30 | Denis Klok v Sasa Markovic | 1-6,7-6,6-0 |
| ITF - Doboj M15 | 2023/05/10 08:00 | Denis Klok v Maximilian Figl | 6-2,6-3 |
| ITF - Kursumlijska Banja M15 | 2023/04/29 09:35 | Denis Klok v Duje Ajdukovic | 3-6,1-6 |
| ITF - Kursumlijska Banja M15 | 2023/04/28 09:50 | Miha Vetrih v Denis Klok | 4-6,2-6 |
| ITF - Kursumlijska Banja M15 | 2023/04/27 07:00 | Marko Andrejic v Denis Klok | 2-6,4-6 |
| ITF - Pazardzhik M15 | 2023/05/20 09:45 | Alex Knaff v Iliyan Radulov | 4-6,2-6 |
| ITF - Pazardzhik M15 | 2023/05/19 08:00 | Iliyan Radulov v Vlad Andrei Dancu | 1-6,6-1,6-2 |
| ITF - Pazardzhik M15 | 2023/05/18 14:40 | Victorio Marquiselli v Iliyan Radulov | 1-6,3-6 |
| ITF - Kursumlijska Banja M25 | 2023/05/10 09:40 | Iliyan Radulov v Mathys Erhard | 3-6,1-6 |
| ITF - Kursumlijska Banja M25 | 2023/05/09 08:00 | Iliyan Radulov v Aleksandar Ljubojevic | 6-3,6-2 |
| ITF - Kursumlijska Banja M25 | 2023/05/08 13:05 | Iliyan Radulov v Pavle Daljev | 6-1,6-2 |
| ITF - Kursumlijska Banja M15 | 2023/05/04 10:10 | Iliyan Radulov v Elliot Benchetrit | 3-6,1-6 |
| ITF - Kursumlijska Banja M15 | 2023/05/03 10:40 | Iliyan Radulov v Chukang Wang | 6-3,6-3 |