Stadium: Court 3 Round: 25 Ground: Clay
| 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 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 Pazardzhik | 2023/05/19 10:15 | Riccardo Balzerani v Marco Miceli | 1-6,2-6 |
| ITF M15 Pazardzhik | 2023/05/18 08:55 | Riccardo Balzerani v Vadym Konovchuk | 6-1,6-0 |
| Challenger Roseto | 2023/04/18 12:00 | Sumit Nagal v Riccardo Balzerani | 6-3,6-3 |
| Challenger Roseto | 2023/04/16 09:45 | Riccardo Balzerani v Khumoyun Sultanov | 6-3,6-3 |
| Challenger Zadar | 2023/03/19 09:00 | Riccardo Balzerani v Carlos Sanchez Jover | 3-6,5-7 |
| ITF M15 Rovinj | 2023/03/16 09:00 | Sergi Perez Contri v Riccardo Balzerani | 6-1,6-2 |
| ITF M15 Rovinj | 2023/03/15 12:55 | Riccardo Balzerani v Dusan Obradovic | 6-3,7-5 |
| ITF M15 Porec | 2023/03/11 14:00 | Mirko Martinez v Riccardo Balzerani | 7-6,6-4 |