Stadium: Court 1 Round: 27 Ground: Clay
| 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 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 | 2023/05/10 09:05 | Calin Manda v Deney Wassermann | 4-6,4-6 |
| ITF M15 Antalya | 2023/05/03 07:30 | Gabriel Debru v Deney Wassermann | 6-7,6-2,6-2 |
| ITF M15 Meerbusch | 2023/04/29 13:15 | Arthur Reymond v Deney Wassermann | 6-3,6-2 |
| ITF M15 Meerbusch | 2023/04/28 10:40 | Deney Wassermann v Philip Florig | 6-1,6-4 |
| ITF M15 Meerbusch | 2023/04/27 11:10 | Matthew William Donald v Deney Wassermann | 2-6,3-6 |
| ITF M15 Meerbusch | 2023/04/26 16:10 | Jeremy Jahn v Deney Wassermann | 6-7,6-7 |
| ITF M15 Antalya | 2023/04/12 10:00 | Deney Wassermann v Vlad Andrei Dancu | 3-6,6-2,6-7 |
| ITF M15 Antalya | 2023/04/11 09:35 | Deney Wassermann v Stefano Reitano | 6-3,6-2 |