Stadium: Court 1 Round: 14 Ground: Clay
| Challenger Perugia | 2023/06/11 11:40 | Bogdan Bobrov v Francesco Forti | 3-6,4-6 |
| ITF M25 Kursumlijska Banja | 2023/06/07 14:45 | Alexander Zgirovsky v Bogdan Bobrov | 6-3,6-2 |
| ITF M25 Kiseljak | 2023/06/03 08:00 | Kirill Kivattsev v Bogdan Bobrov | 7-6,7-6 |
| ITF M25 Kiseljak | 2023/06/01 16:50 | Andrej Nedic v Bogdan Bobrov | 6-3,6-7,6-7 |
| ITF M25 Kiseljak | 2023/05/31 07:00 | Tomas Lanik v Bogdan Bobrov | 6-4,3-6,6-7 |
| Challenger Skopje | 2023/05/22 09:00 | Sumit Nagal v Bogdan Bobrov | 6-0,6-2 |
| Challenger Skopje | 2023/05/21 10:35 | Mikalai Haliak v Bogdan Bobrov | 5-7,4-6 |
| ITF M15 Monastir | 2023/05/06 10:25 | Omni Kumar v Bogdan Bobrov | 2-6,6-2,7-6 |
| ITF M15 Kursumlijska Banja | 2023/06/13 15:55 | Iliyan Radulov v Gabriel Donev | 2-6,4-6 |
| ITF M15 Pazardzhik | 2023/05/24 08:45 | Iliyan Radulov v Riccardo Balzerani | 4-6,1-6 |
| ITF M15 Pazardzhik | 2023/05/21 12:30 | Iliyan Radulov v Simone Roncalli | 6-4,6-1 |
| ITF M15 Pazardzhik | 2023/05/21 07:00 | Denis Klok v Iliyan Radulov | 1-6,1-6 |
| ITF M15 Pazardzhik | 2023/05/20 09:45 | Alex Knaff v Iliyan Radulov | 4-6,2-6 |
| ITF M15 Pazardzhik | 2023/05/19 08:00 | Iliyan Radulov v Vlad Andrei Dancu | 1-6,6-1,6-2 |
| ITF M15 Pazardzhik | 2023/05/18 14:40 | Victorio Marquiselli v Iliyan Radulov | 1-6,3-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:40 | Iliyan Radulov v Mathys Erhard | 3-6,1-6 |