Stadium: Court 4 Round: 26 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/06/18 09:30 | Felix Gill v Viktor Jovic | 6-4,3-6,4-10 |
| ITF M15 Kursumlijska Banja | 2023/06/17 19:00 | Andrey Chepelev v Felix Gill | 6-7,3-6 |
| ITF M15 Kursumlijska Banja | 2023/06/13 14:50 | David Prasievi v Felix Gill | 2-6,0-6 |
| ITF M15 Sarajevo | 2023/06/08 10:05 | Felix Gill v Matej Dodig | 3-6,3-6 |
| ITF M15 Sarajevo | 2023/06/06 11:30 | Felix Gill v Tarik Bajrovic | 6-1,6-0 |
| ITF M15 Kursumlijska Banja | 2023/05/31 14:15 | Felix Gill v Martyn Pawelski | 6-7,4-6 |
| ITF M25 Gurb | 2023/05/19 11:35 | Felix Gill v Daniel Cukierman | 4-6,4-6 |
| ITF M25 Gurb | 2023/05/18 12:30 | Felix Gill v Noah Lopez | 7-5,6-2 |
| 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 |