Stadium: Court 3 Round: 29 Ground: Clay
| 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 |
| ITF M25 Kursumlijska Banja | 2023/05/08 13:05 | Iliyan Radulov v Pavle Daljev | 6-1,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/04 10:10 | Iliyan Radulov v Elliot Benchetrit | 3-6,1-6 |
| ITF M15 Pazardzhik | 2023/05/21 07:00 | Simon A Ivanov v Simone Roncalli | 3-6,6-3,4-6 |
| ITF M15 Pazardzhik | 2023/05/20 07:00 | Simone Roncalli v Oleg Prihodko | 6-4,6-3 |
| ITF M15 Pazardzhik | 2023/05/19 08:20 | Simone Roncalli v Luigi Sorrentino | 6-1,4-6,7-5 |
| ITF M15 Pazardzhik | 2023/05/18 12:45 | Simone Roncalli v Sean Hess | 7-6,6-2 |
| Challenger Francavilla | 2023/05/07 09:00 | Simone Roncalli v Alexander Weis | 7-5,4-6,3-6 |
| ITF M15 Monastir | 2023/03/28 09:30 | Simone Roncalli v Benjamin Pietri | 4-6,1-6 |
| ITF M15 Monastir | 2023/03/24 08:30 | Ray Ho v Simone Roncalli | 6-7,6-2,6-3 |
| ITF M15 Monastir | 2023/03/23 12:20 | Alexis Boureau v Simone Roncalli | 1-6,6-4,4-6 |