Stadium: Court 1 Round: 14 Ground: Clay
| 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 Monastir | 2023/05/05 09:50 | Thomas Braithwaite v Bogdan Bobrov | 3-6,6-7 |
| ITF M15 Monastir | 2023/05/04 11:55 | Adrian Oetzbach v Bogdan Bobrov | 4-6,4-6 |
| ITF M15 Monastir | 2023/05/03 12:00 | Derek Pham v Bogdan Bobrov | 2-6,2-6 |
| ITF M15 Monastir | 2023/04/28 09:00 | Bogdan Bobrov v Andrea Guerrieri | 7-6,4-6,2-6 |
| ITF M15 Monastir | 2023/04/27 08:30 | Bogdan Bobrov v Maxence Rivet | 6-3,6-3 |
| 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 |
| ITF M25 Kursumlijska Banja | 2023/05/09 08:00 | Iliyan Radulov v Aleksandar Ljubojevic | 6-3,6-2 |