Stadium: Stadium Court Round: 25 Ground: Clay
| Orlando, USA | 2021/04/15 16:30 | Gunneswaran, Prajnesh v Sock, Jack | 3-6,4-6 |
| Orlando, USA | 2021/04/13 16:20 | Gunneswaran, Prajnesh v Ebden, Matthew | 6-4,6-1 |
| ATP - Dubaï | 2021/03/13 07:00 | Bhambri, Yuki v Gunneswaran, Prajnesh | 6-1,6-4 |
| Nur Sultan, Kazakhstan | 2021/03/06 06:35 | Tomas Machac v Gunneswaran, Prajnesh | 6-3,1-6,6-2 |
| Nur Sultan, Kazakhstan | 2021/03/05 05:00 | James Duckworth v Gunneswaran, Prajnesh | 4-6,6-2,6-7 |
| Nur Sultan, Kazakhstan | 2021/03/02 04:00 | Lenz, Julian v Gunneswaran, Prajnesh | 6-3,2-6,3-6 |
| Nur Sultan, Kazakhstan | 2021/02/27 06:25 | Gunneswaran, Prajnesh v Jurij Rodionov | 2-6,6-3,3-6 |
| Nur Sultan, Kazakhstan | 2021/02/26 07:40 | Martin Klizan v Gunneswaran, Prajnesh | 3-6,6-4,4-6 |
| Challenger - Santiago | 2021/03/16 15:15 | Nicolas Alvarez v Pedro Sakamoto | 3-6,6-4,6-3 |
| ATP - Santiago | 2021/03/07 14:00 | Alejandro Tabilo v Pedro Sakamoto | 7-6,6-4 |
| ATP - Santiago | 2021/03/06 13:00 | Matos, Rafael v Pedro Sakamoto | 3-6,1-6 |
| ATP - Buenos Aires | 2021/02/28 14:00 | Pedro Sakamoto v Velotti, Agustin | 3-6,4-6 |
| ATP - Cordoba | 2021/02/22 17:30 | Facundo Bagnis v Pedro Sakamoto | 6-2,6-4 |
| ATP - Cordoba | 2021/02/21 16:20 | Renzo Olivo v Pedro Sakamoto | 2-6,5-7 |
| ATP - Cordoba | 2021/02/20 17:25 | Pedro Sakamoto v Emilio Gomez | 3-6,6-1,7-6 |
| Challenger - Concepcion | 2021/02/18 15:00 | Pedro Sakamoto v Martin, Andrej | 3-6,3-6 |