stadio: Court 1 Round: 27 Ground: Clay
| ITF M25 Saragozza | 2023/10/05 14:30 | Alvaro Lopez San Martin v Iliyan Radulov | 6-7,6-2,4-6 |
| ITF M25 Saragozza | 2023/10/03 10:30 | Oscar Jose Gutierrez v Iliyan Radulov | 1-6,6-7 |
| ITF M25 Sabadell | 2023/09/28 13:05 | Felix Gill v Iliyan Radulov | 6-3,6-2 |
| ITF M25 Sabadell | 2023/09/26 15:30 | Albert Pedrico Kravtsov v Iliyan Radulov | 3-6,1-6 |
| Challenger Parma | 2023/06/18 08:00 | Bogdan Bobrov v Iliyan Radulov | 4-6,6-2,6-4 |
| 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 M25 Saragozza | 2023/10/05 09:00 | Deney Wassermann v Alex M Pujolras | 6-3,6-4 |
| ITF M25 Saragozza | 2023/10/04 10:30 | Enrique G Sanchez v Deney Wassermann | 2-6,3-6 |
| ITF M15 Buschhausen | 2023/09/14 12:05 | Deney Wassermann v Thiemo De Bakker | 3-6,2-6 |
| ITF M15 Buschhausen | 2023/09/12 09:45 | Alec Beckley v Deney Wassermann | 2-6,4-6 |
| ITF M15 Haren | 2023/09/06 12:55 | Deney Wassermann v Brian Bozemoj | 6-3,6-7,5-7 |
| ITF M25 Oldenzaal | 2023/08/31 07:55 | Deney Wassermann v Max Houkes | 7-6,4-6,3-6 |
| Challenger Amersfoort | 2023/07/16 10:30 | Joris De Loore v Deney Wassermann | 7-6,6-4 |
| ITF M25 L'Aia | 2023/07/07 12:35 | Sander Jong v Deney Wassermann | 3-6,6-7 |