Stadium: Court 2 Round: 25 Ground: Clay
| ITF M25 Bělehrad | 2021/06/30 11:30 | Pedja Krstin v Bogdan Pavel | 6-1,6-1 |
| Challenger Milán | 2021/06/25 13:50 | Pedja Krstin v Hugo Grenier | 4-6,4-6 |
| Challenger Milán | 2021/06/23 11:00 | Pedja Krstin v Manuel Guinard | 6-4,0-6,6-4 |
| Challenger Almaty | 2021/06/09 05:40 | Evan Furness v Pedja Krstin | 6-3,6-1 |
| Challenger Almaty | 2021/06/07 11:30 | Pedja Krstin v Mohamed Safwat | 6-4,6-0 |
| ATP Bělehrad | 2021/05/25 13:55 | Alex Molcan v Pedja Krstin | 6-0,6-0 |
| ATP Bělehrad | 2021/05/23 10:30 | Pedja Krstin v Soonwoo Kwon | 6-2,3-6,6-1 |
| ITF M15 Prijedor | 2021/05/11 15:05 | Pedja Krstin v Mateja Janicijevic | 6-1,6-0 |
| Challenger Perugia | 2021/07/07 13:50 | Dimitar Kuzmanov v Nerman Fatic | 4-6,6-7 |
| Challenger Perugia | 2021/07/05 19:00 | Federico Gaio v Dimitar Kuzmanov | 6-2,3-6,6-7 |
| Wimbledon | 2021/06/22 10:00 | Marius Copil v Dimitar Kuzmanov | 6-4,6-3 |
| Challenger Almaty | 2021/06/11 04:30 | Chun Hsin Tseng v Dimitar Kuzmanov | 7-6,6-3 |
| Challenger Almaty | 2021/06/10 04:00 | Dimitar Kuzmanov v Enzo Couacaud | 7-5,6-0 |
| 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 |