Stadium: Court Lisboa Round: 27 Ground: Clay
| Challenger - Banja Luka | 2018/09/13 08:30 | Dimitar Kuzmanov v Alessandro Giannessi | 6-2,2-6,2-6 |
| Challenger - Lissabon | 2020/10/14 09:00 | Benjamin Bonzi v Dimitar Kuzmanov | 5-7,2-6 |
| Challenger - Lissabon | 2020/10/12 11:10 | Frederico Ferreira Silva v Dimitar Kuzmanov | 5-7,3-6 |
| Challenger - Lissabon | 2020/10/10 14:30 | Dimitar Kuzmanov v Stefano Napolitano | 6-2,4-6,6-1 |
| Challenger - Split | 2020/09/26 14:00 | Orlando Luz v Dimitar Kuzmanov | 6-2,6-4 |
| ITF M25 - Klosters | 2020/09/16 11:00 | Holger Rune v Dimitar Kuzmanov | 2-6,6-1,6-1 |
| ITF M25 - Poznan | 2020/08/30 08:50 | Kacper Zuk v Dimitar Kuzmanov | 7-6,6-1 |
| ITF M25 - Poznan | 2020/08/29 11:05 | Jelle Sels v Dimitar Kuzmanov | 7-5,3-6,4-6 |
| ITF M25 - Poznan | 2020/08/28 12:25 | Dimitar Kuzmanov v Nino Serdarusic | 6-4,6-3 |
| Challenger - Lissabon | 2020/10/14 10:55 | Alessandro Giannessi v Paolo Lorenzi | 7-5,6-3 |
| Challenger - Lissabon | 2020/10/12 09:00 | Alessandro Giannessi v Roberto Cid Subervi | 6-3,5-7,6-2 |
| Challenger - Barcelona | 2020/10/07 10:15 | Maxime Janvier v Alessandro Giannessi | 6-4,3-6,6-2 |
| Challenger - Barcelona | 2020/10/06 08:00 | Peter Polansky v Alessandro Giannessi | 2-6,4-6 |
| Challenger - Split | 2020/10/02 11:00 | Alessandro Giannessi v Borna Gojo | 3-6,3-6 |
| Challenger - Split | 2020/09/29 12:45 | Nino Serdarusic v Alessandro Giannessi | 4-6,4-6 |
| French Open | 2020/09/23 11:10 | Marc Polmans v Alessandro Giannessi | 5-7,6-4,6-3 |
| French Open | 2020/09/21 09:20 | Danilo Petrovic v Alessandro Giannessi | 4-6,6-7 |