Stadium: Center Court Round: 19 Ground: Clay
| ITF M25 Kursumlijska Banja | 2023/05/08 13:05 | Iliyan Radulov v Pavle Daljev | 6-1,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/04 10:10 | Iliyan Radulov v Elliot Benchetrit | 3-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/05/03 10:40 | Iliyan Radulov v Chukang Wang | 6-3,6-3 |
| ITF M15 Antalya | 2023/03/07 12:55 | Iliyan Radulov v Nicolas Zanellato | 6-7,2-6 |
| ITF M15 Antalya | 2023/03/02 08:35 | Iliyan Radulov v Eric Vanshelboim | 6-7,4-6 |
| ITF M15 Antalya | 2023/03/01 07:00 | Vilius Gaubas v Iliyan Radulov | 1-6,6-4,1-6 |
| ITF M15 Antalya | 2023/02/22 07:00 | Denis Klok v Iliyan Radulov | 6-3,6-0 |
| ITF M15 Sozopol | 2022/10/11 07:00 | Iliyan Radulov v Alexander Donski | 6-4,6-7,4-6 |
| ITF M25 Kursumlijska Banja | 2023/05/08 14:25 | Aleksandar Ljubojevic v Mihail Ivanov | 4-6,6-2,10-2 |
| ITF M15 Kursumlijska Banja | 2023/05/01 10:05 | Matvey Minin v Aleksandar Ljubojevic | 6-3,6-1 |
| ITF M15 Kursumlijska Banja | 2023/04/30 07:00 | Aleksandar Ljubojevic v Aleksa Smiljanic | 6-4,6-1 |
| ITF M25 Pirot | 2022/09/18 12:30 | Aleksandar Ljubojevic v Sasa Markovic | 1-6,7-5,7-10 |
| ITF M15 Zlatibor | 2022/09/12 10:00 | Valerio Perruzza v Aleksandar Ljubojevic | 7-6,7-5 |
| UTR Pro Tennis Series Nis | 2021/10/09 13:15 | Aleksandar Ljubojevic v Vladimir Popov | 4-6,5-7 |
| UTR Pro Tennis Series Nis | 2021/10/07 07:00 | Aleksandar Ljubojevic v Andrey Chepelev | 2-6,2-6 |
| UTR Pro Tennis Series Nis | 2021/10/06 07:00 | Aleksandar Ljubojevic v Egor Novikov | 5-7,6-4,6-3 |