| UTR Pro Tennis Series Sofia | 2021/09/01 08:00 | Denislav Prodanov v Josh Sheehy | 3-6,0-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 08:00 | Denislav Prodanov v Mario Radev | 6-1,1-6,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 07:00 | Christos Keisidis v Denislav Prodanov | 6-1,5-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 09:00 | Denislav Prodanov v Valentin Vanta | 2-6,3-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 07:30 | Petyr Kardzhiev v Denislav Prodanov | 0-6,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 10:30 | Iliyan Radulov v Denislav Prodanov | 2-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 09:00 | Dian Nedev v Denislav Prodanov | 6-7,4-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 07:30 | Denislav Prodanov v Ilya Snitari | 1-6,1-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 06:30 | Volodymyr Uzhylovskyi v George Lazarov | 1-6,6-1,1-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Volodymyr Uzhylovskyi v Warren Sinius | 6-2,5-4 |
| UTR Pro Tennis Series Sofia | 2021/08/30 13:30 | Valentin Vanta v Volodymyr Uzhylovskyi | 6-2,6-3 |
| UTR Pro Tennis Series Portoroz | 2021/08/27 12:00 | Vladan Tadic v Volodymyr Uzhylovskyi | 5-7,2-6 |
| UTR Pro Tennis Series Portoroz | 2021/08/26 07:00 | Nik Razborsek v Volodymyr Uzhylovskyi | 6-3,5-7,5-7 |
| UTR Pro Tennis Series Portoroz | 2021/08/25 10:00 | Olexiy Kolisnyk v Volodymyr Uzhylovskyi | 6-1,6-1 |
| UTR Pro Tennis Series Portoroz | 2021/08/17 12:30 | Volodymyr Uzhylovskyi v Max Lukman | 6-1,5-1 |
| ITF M15 Cairo | 2021/08/02 11:30 | Volodymyr Uzhylovskyi v Lautaro Agustin Falabella | 2-6,6-2,10-12 |