Stadion: Court 1 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 - Sozopol | 2021/10/10 09:00 | Ivan Penev v Gianluca Coloma-Heck | 6-1,6-3 |
| ITF - M15 - Sozopol | 2021/10/04 07:00 | Yann Wojcik v Ivan Penev | 3-6,7-5,10-2 |
| ITF - M15 - Sozopol | 2021/09/13 10:30 | Tommaso Compagnucci v Ivan Penev | 6-2,6-3 |
| ITF - M15 - Sozopol | 2021/09/12 10:00 | Radu F Macovei v Ivan Penev | 4-6,3-6 |
| UTR Pro Tennis Series - Sofia | 2021/09/01 11:00 | Samuil Konov v Ivan Penev | 4-6,6-1,6-0 |
| UTR Pro Tennis Series - Sofia | 2021/08/31 06:30 | Martin Dimitrov v Ivan Penev | 1-6,6-3,6-3 |
| UTR Pro Tennis Series - Sofia | 2021/08/30 11:15 | Matias Zukas v Ivan Penev | 7-5,6-3 |
| UTR Pro Tennis Series - Sofia | 2021/08/29 12:30 | Ivan Penev v Alexandru Luca | 6-1,6-4 |
| ITF - M15 - Sozopol | 2021/10/10 09:00 | Nikola Kolyachev v Berk Ilkel | 0-6,1-6 |
| ITF - M15 - Sozopol | 2021/10/06 10:50 | Ilya Snitari v Berk Ilkel | 3-6,6-4,6-0 |
| ITF - M15 - Sozopol | 2021/10/05 06:30 | Berk Ilkel v Plamen Milushev | 6-3,7-5 |
| ITF - M15 - Sozopol | 2021/10/03 09:00 | Berk Ilkel v Enes Donmezer | 3-6,7-6,10-7 |
| Challenger - Istanbul | 2021/09/12 09:50 | Berk Ilkel v Alexander Shevchenko | 1-6,3-6 |
| ITF - M15 - Novi Sad | 2021/08/02 08:00 | Berk Ilkel v Milan Drinic | 2-6,1-6 |
| ITF - M15 - Novi Sad | 2021/07/25 12:00 | Aleksa Mardjonovic v Berk Ilkel | 6-2,7-5 |
| ITF - M15 - Monastir | 2021/06/27 09:00 | Berk Ilkel v Brandon Lam | 6-2,6-7,5-10 |