Stadium: Court 1 Round: 27 Ground: Clay
| 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 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 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 The Hague | 2023/07/07 12:35 | Sander Jong v Deney Wassermann | 3-6,6-7 |
| ITF M25 The Hague | 2023/07/06 17:00 | Thiemo De Bakker v Deney Wassermann | 6-7,6-1,4-6 |
| ITF M25 The Hague | 2023/07/05 17:40 | Deney Wassermann v Ergi Kirkin | 7-6,7-6 |
| ITF M15 Alkmaar | 2023/06/28 11:30 | Deney Wassermann v Guy Den Ouden | 6-7,5-7 |
| ITF M15 Antalya | 2023/05/13 07:55 | Deney Wassermann v Gabriel Debru | 6-3,6-4 |