Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| Australian Open | 2021/01/12 13:10 | Prajnesh Gunneswaran v Constant Lestienne | 2-6,3-6 |
| Australian Open | 2021/01/11 12:20 | Prajnesh Gunneswaran v Brayden Schnur | 6-4,4-6,6-2 |
| Challenger Orlando | 2020/11/22 16:00 | Brandon Nakashima v Prajnesh Gunneswaran | 6-3,6-4 |
| Challenger Orlando | 2020/11/21 16:00 | Prajnesh Gunneswaran v Christopher Eubanks | 6-4,7-6 |
| Challenger Orlando | 2020/11/20 15:00 | Dmitry Popko v Prajnesh Gunneswaran | 0-6,3-6 |
| Challenger Orlando | 2020/11/17 17:00 | Sadio Doumbia v Prajnesh Gunneswaran | 3-6,5-7 |
| Challenger Cary | 2020/11/15 17:00 | Prajnesh Gunneswaran v Denis Kudla | 6-3,3-6,0-6 |
| Challenger Cary | 2020/11/13 18:20 | Prajnesh Gunneswaran v Thomaz Bellucci | 3-6,7-5,7-6 |
| Challenger Antalya | 2021/02/01 11:30 | Dimitar Kuzmanov v Facundo Mena | 6-2,4-6,0-6 |
| Challenger Antalya Qual | 2021/01/31 07:00 | Zdenek Kolar v Dimitar Kuzmanov | 3-6,4-6 |
| Challenger Antalya Qual | 2021/01/28 06:30 | Akira Santillan v Dimitar Kuzmanov | 6-4,4-6,7-6 |
| ATP Antalya | 2021/01/10 11:10 | Matteo Berrettini v Dimitar Kuzmanov | 6-2,6-3 |
| ATP Antalya | 2021/01/07 07:00 | Andrea Pellegrino v Dimitar Kuzmanov | 6-4,6-7,5-7 |
| ATP Antalya | 2021/01/06 11:55 | Mirza Basic v Dimitar Kuzmanov | 3-6,1-6 |
| ATP Sofia | 2020/11/09 16:05 | Salvatore Caruso v Dimitar Kuzmanov | 4-6,6-4,6-4 |
| Challenger Parma 2 | 2020/10/31 11:30 | Dimitar Kuzmanov v Luca Vanni | 5-7,6-3,1-6 |