| 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 |
| ITF M15 Sofia | 2021/07/07 07:00 | Timo Legout v Denislav Prodanov | 6-0,7-6 |
| ITF M15 Sofia | 2021/07/05 07:00 | Denislav Prodanov v Mihnea L.S. Turcu | 6-0,6-0 |
| UTR Pro Tennis Series Sofia | 2021/08/30 10:45 | Mario Radev v Josh Sheehy | 1-6,2-6 |
| UTR Pro Tennis Series Sofia | 2021/08/29 12:00 | George Lazarov v Mario Radev | 6-0,6-1 |