Stadium: Court 1 Round: 14 Ground: Clay
| ITF - Monastir M15 | 2021/03/15 12:30 | Stefano Reitano v Luigi Sorrentino | 4-6,2-6 |
| ITF - Monastir M15 | 2021/03/15 08:00 | Stefano Reitano v Youcef Rihane | 3-6,6-3,10-6 |
| ITF - Monastir M15 | 2021/03/14 09:00 | Juan Ignacio Galarza v Stefano Reitano | 2-6,2-6 |
| ITF - Monastir M15 | 2021/03/07 09:00 | Stefano Reitano v Buvaysar Gadamauri | 5-7,6-4,5-10 |
| ITF - Monastir M15 | 2021/03/03 13:20 | Stefano Reitano v Naoki Tajima | 1-6,0-6 |
| ITF - Monastir M15 | 2021/03/01 13:00 | Stefano Reitano v Christian Hansen | 7-6,6-2 |
| ITF - Monastir M15 | 2021/03/01 09:00 | Stefano Reitano v Leonardo Taddia | 6-1,6-0 |
| ITF - Monastir M15 | 2021/02/28 10:30 | Niklas Guttau v Stefano Reitano | 3-6,6-3,7-10 |
| Challenger Oeiras | 2021/04/07 14:00 | Dimitar Kuzmanov v Ernesto Escobedo | 6-2,6-2 |
| Challenger Oeiras | 2021/04/05 12:25 | Dimitar Kuzmanov v Lucas Miedler | 6-1,6-0 |
| Challenger Zadar | 2021/03/28 10:00 | Nikola Milojevic v Dimitar Kuzmanov | 2-6,6-2,7-6 |
| Challenger Zadar | 2021/03/26 11:40 | Dimitar Kuzmanov v Blaz Kavcic | 6-4,6-1 |
| 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 Dubaj | 2021/03/13 10:05 | Emil Ruusuvuori v Dimitar Kuzmanov | 7-6,4-6,6-1 |
| Puchar Davisa | 2021/03/06 16:00 | Dimitar Kuzmanov v Gerardo L Villasenor | 6-7,6-4,6-7 |