Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| Open d'Australie | 2021/01/12 13:10 | Gunneswaran, Prajnesh v Constant Lestienne | 2-6,3-6 |
| Open d'Australie | 2021/01/11 12:20 | Gunneswaran, Prajnesh v Schnur, Brayden | 6-4,4-6,6-2 |
| Orlando, USA | 2020/11/22 16:00 | Brandon Nakashima v Gunneswaran, Prajnesh | 6-3,6-4 |
| Orlando, USA | 2020/11/21 16:00 | Gunneswaran, Prajnesh v Christopher Eubanks | 6-4,7-6 |
| Orlando, USA | 2020/11/20 15:00 | Dmitry Popko v Gunneswaran, Prajnesh | 0-6,3-6 |
| Orlando, USA | 2020/11/17 17:00 | Doumbia, Sadio v Gunneswaran, Prajnesh | 3-6,5-7 |
| Challenger Cary | 2020/11/15 17:00 | Gunneswaran, Prajnesh v Denis Kudla | 6-3,3-6,0-6 |
| Challenger Cary | 2020/11/13 18:20 | Gunneswaran, Prajnesh v Bellucci, Thomaz | 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 |
| Antalya, Turquie | 2021/01/10 11:10 | Matteo Berrettini v Dimitar Kuzmanov | 6-2,6-3 |
| Antalya, Turquie | 2021/01/07 07:00 | Andrea Pellegrino v Dimitar Kuzmanov | 6-4,6-7,5-7 |
| Antalya, Turquie | 2021/01/06 11:55 | Mirza Basic v Dimitar Kuzmanov | 3-6,1-6 |
| Sofia, Bulgaria | 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 Vanni, Luca | 5-7,6-3,1-6 |