Stadium: Court 7 Round: 62 Ground: Clay
| ITF - M25 Benicarlo | 2023/11/05 08:30 | Iliyan Radulov v Joris Moret | 7-5,6-4 |
| ITF M25 - Zaragoza | 2023/10/06 08:30 | Iliyan Radulov v Deney Wassermann | 4-6,4-6 |
| ITF M25 - Zaragoza | 2023/10/05 14:30 | Alvaro Lopez San Martin v Iliyan Radulov | 6-7,6-2,4-6 |
| ITF M25 - Zaragoza | 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 - M25 Benicarlo | 2023/11/05 14:30 | Kirill Mishkin v Tancredi Alfano | 6-1,7-5 |
| ITF - M15 Telavi | 2023/10/25 07:30 | Pietro Pampanin v Kirill Mishkin | 6-7,6-3,6-1 |
| ITF - M25 Telavi | 2023/10/23 06:00 | Kirill Mishkin v Eskander Guryev | 5-7,6-3,10-8 |
| ITF - M15 Castellon | 2023/10/15 10:00 | Kirill Mishkin v Albert Pedrico Kravtsov | 2-6,0-6 |
| ITF - M15 Vigo | 2023/10/09 12:00 | Ian Luca Cervantes Tomas v Kirill Mishkin | 7-5,6-4 |
| ITF - M25 Santa Margherita | 2023/10/03 09:35 | Kirill Mishkin v Gian M Di Natale | 4-6,2-6 |
| ITF - M25 Santa Margherita | 2023/09/26 10:10 | Francesco Forti v Kirill Mishkin | 6-1,6-0 |
| ITF - M25 Santa Margherita | 2023/09/19 09:25 | Manuel Plunger v Kirill Mishkin | 6-4,6-0 |