Stadium: Court 1 Round: 26 Ground: Clay
| Challenger Almaty | 2021/06/08 06:00 | Dimitar Kuzmanov v Adrian Menendez-Maceiras | 6-2,6-4 |
| French Open | 2021/05/24 20:40 | Hugo Dellien v Dimitar Kuzmanov | 3-6,6-2,6-1 |
| Challenger Biella | 2021/05/19 09:00 | Dimitar Kuzmanov v Facundo Mena | 2-6,7-6,1-6 |
| Challenger Biella | 2021/05/17 10:10 | Tristan Lamasine v Dimitar Kuzmanov | 5-7,6-4,1-6 |
| Challenger Zagreb | 2021/05/09 08:30 | Zhizhen Zhang v Dimitar Kuzmanov | 4-6,6-2,6-3 |
| Challenger Biella | 2021/05/05 08:00 | Dimitar Kuzmanov v Juan Pablo Varillas | 1-6,7-5,6-7 |
| Challenger Biella | 2021/05/04 08:00 | Dimitar Kuzmanov v Lorenzo Giustino | 6-3,1-6,6-3 |
| Challenger Biella | 2021/05/03 08:30 | Viktor Galovic v Dimitar Kuzmanov | 6-4,6-2 |
| Challenger Almaty | 2021/06/08 09:50 | Vitaliy Sachko v Enzo Couacaud | 7-6,5-7,2-6 |
| French Open | 2021/06/02 15:40 | Enzo Couacaud v Pablo Carreno Busta | 6-2,3-6,4-6,4-6 |
| French Open | 2021/05/30 09:00 | Egor Gerasimov v Enzo Couacaud | 6-7,4-6,3-6 |
| Challenger Biella | 2021/05/22 09:30 | Enzo Couacaud v Thanasi Kokkinakis | 3-6,4-6 |
| Challenger Biella | 2021/05/21 10:00 | Tomas Martin Etcheverry v Enzo Couacaud | 1-6,7-5,4-6 |
| Challenger Biella | 2021/05/20 09:30 | Enzo Couacaud v Bjorn Fratangelo | 6-1,6-7,6-3 |
| Challenger Biella | 2021/05/19 11:45 | Enzo Couacaud v Tim Van Rijthoven | 7-6,5-7,6-2 |
| Challenger Biella | 2021/05/17 17:20 | Enzo Couacaud v Tobias Kamke | 6-4,6-2 |