Stadium: Court 1 Round: 27 Ground: Clay
| Challenger - Zadar | 2021/03/25 10:45 | Dimitar Kuzmanov v Zdenek Kolar | 6-4,6-3 |
| Challenger - Zadar | 2021/03/23 12:50 | Gian Marco Moroni v Dimitar Kuzmanov | 4-6,4-6 |
| ATP - Dubai | 2021/03/13 10:05 | Emil Ruusuvuori v Dimitar Kuzmanov | 7-6,4-6,6-1 |
| Davis Cup | 2021/03/06 16:00 | Dimitar Kuzmanov v Gerardo L Villasenor | 6-7,6-4,6-7 |
| Davis Cup | 2021/03/05 14:00 | Dimitar Kuzmanov v Luis Patino | 6-1,6-1 |
| Challenger Potchefstroom | 2021/02/19 08:00 | Dimitar Kuzmanov v Lucas Miedler | 7-5,2-6,2-6 |
| Challenger Potchefstroom | 2021/02/17 10:30 | Dimitar Kuzmanov v Tristan Lamasine | 7-5,7-6 |
| Challenger Potchefstroom | 2021/02/15 13:05 | Jay Clarke v Dimitar Kuzmanov | 7-5,3-6,6-7 |
| Challenger - Zadar | 2021/03/24 09:00 | Blaz Kavcic v Alex Molcan | 6-2,6-1 |
| Challenger - Zadar | 2021/03/22 12:45 | Blaz Kavcic v Andrea Pellegrino | 6-3,6-1 |
| Challenger - Gran Canaria | 2021/03/06 14:00 | Blaz Kavcic v Carlos Gimeno Valero | 6-3,1-6,5-7 |
| Challenger - Gran Canaria | 2021/03/05 12:15 | Alex Molcan v Blaz Kavcic | 4-6,5-7 |
| Challenger - Gran Canaria | 2021/03/03 11:00 | Blaz Kavcic v Riccardo Bonadio | 6-2,6-4 |
| Challenger - Gran Canaria | 2021/03/01 14:45 | Blaz Kavcic v Michael Vrbensky | 6-4,6-4 |
| Challenger - Gran Canaria | 2021/02/24 13:35 | Blaz Kavcic v Riccardo Bonadio | 6-4,3-6,3-6 |
| Challenger - Gran Canaria | 2021/02/22 15:20 | Federico Gaio v Blaz Kavcic | 3-6,3-6 |