| UTR Pro Tennis Series Pazardzhik | 2021/07/16 07:30 | Petyr Kardzhiev v Prodanov, Denislav | 0-6,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 10:30 | Iliyan Radulov v Prodanov, Denislav | 2-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 09:00 | Dian Nedev v Prodanov, Denislav | 6-7,4-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 07:30 | Prodanov, Denislav v Ilya Snitari | 1-6,1-6 |
| ITF M15 Sofia | 2021/07/07 07:00 | Timo Legout v Prodanov, Denislav | 6-0,7-6 |
| ITF M15 Sofia | 2021/07/05 07:00 | Prodanov, Denislav v Turcu, Mihnea Lorin Stefan | 6-0,6-0 |
| ITF M15 Sofia | 2021/07/04 06:30 | Obrad Markovski v Prodanov, Denislav | 1-6,7-5,7-10 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 08:30 | Prodanov, Denislav v Faivre, Pierre | 0-6,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 10:30 | Dzhavakian, Yurii v Valentin Vanta | 5-7,3-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 06:00 | Petr Nesterov v Valentin Vanta | 6-2,6-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/14 09:00 | Arthus De La Bassetiere v Valentin Vanta | 3-6,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 10:30 | Lazov, Alexander v Valentin Vanta | 7-6,2-6,4-6 |
| ITF M15 Sofia | 2021/07/04 06:30 | Matteo De Vincentis v Valentin Vanta | 6-4,6-0 |
| ITF M25 Belgrade | 2021/06/27 09:00 | Valentin Vanta v Aleksa Mardjonovic | 5-7,3-6 |
| UTR Pro Tennis Series Bucharest | 2021/06/06 06:00 | Yanais Laurent v Valentin Vanta | 2-6,1-5 |
| UTR Pro Tennis Series Bucharest | 2021/06/05 10:00 | Ioan Alexandru Chirita v Valentin Vanta | 2-6,6-3,4-6 |