Stadium: Court 5 Round: 25 Ground: Clay
| 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 Kursumlijska Banja | 2023/05/03 10:40 | Iliyan Radulov v Chukang Wang | 6-3,6-3 |
| ITF - M15 Antalya | 2023/03/07 12:55 | Iliyan Radulov v Nicolas Zanellato | 6-7,2-6 |
| ITF - M15 Antalya | 2023/03/02 08:35 | Iliyan Radulov v Eric Vanshelboim | 6-7,4-6 |
| ITF - M15 Antalya | 2023/03/01 07:00 | Vilius Gaubas v Iliyan Radulov | 1-6,6-4,1-6 |
| ITF - M15 Antalya | 2023/02/22 07:00 | Denis Klok v Iliyan Radulov | 6-3,6-0 |
| ITF - M25 Santa Margherita | 2023/04/27 08:25 | Jaime Faria v Mathys Erhard | 6-4,3-6,6-4 |
| ITF - M25 Santa Margherita | 2023/04/26 08:00 | Marcello Serafini v Mathys Erhard | 1-6,2-6 |
| ITF - M25 Santa Margherita | 2023/04/24 08:00 | Giorgio Tabacco v Mathys Erhard | 6-4,5-7,2-6 |
| ITF - M25 Santa Margherita | 2023/04/21 09:00 | Tommaso Compagnucci v Mathys Erhard | 3-6,7-6,6-2 |
| ITF - M25 Santa Margherita | 2023/04/20 08:00 | Mathys Erhard v Lorenzo Rottoli | 6-0,6-4 |
| ITF - M25 Santa Margherita | 2023/04/19 08:00 | Mathys Erhard v Alexander Orlov | 6-4,6-2 |
| ITF - M25 Santa Margherita | 2023/04/17 14:00 | Mathys Erhard v Daniel Bagnolini | 6-3,6-1 |
| ITF - M25 Santa Margherita | 2023/04/12 10:30 | Kyle Edmund v Mathys Erhard | 7-6,3-6,6-1 |