Stadium: Stadium Court Round: 25 Ground: Clay
| Challenger Orlando | 2021/04/15 16:30 | Prajnesh Gunneswaran v Jack Sock | 3-6,4-6 |
| Challenger Orlando | 2021/04/13 16:20 | Prajnesh Gunneswaran v Matthew Ebden | 6-4,6-1 |
| ATP Dubai | 2021/03/13 07:00 | Yuki Bhambri v Prajnesh Gunneswaran | 6-1,6-4 |
| Challenger Nur-Sultan | 2021/03/06 06:35 | Tomas Machac v Prajnesh Gunneswaran | 6-3,1-6,6-2 |
| Challenger Nur-Sultan | 2021/03/05 05:00 | James Duckworth v Prajnesh Gunneswaran | 4-6,6-2,6-7 |
| Challenger Nur-Sultan | 2021/03/02 04:00 | Julian Lenz v Prajnesh Gunneswaran | 6-3,2-6,3-6 |
| Challenger Nur-Sultan | 2021/02/27 06:25 | Prajnesh Gunneswaran v Jurij Rodionov | 2-6,6-3,3-6 |
| Challenger Nur-Sultan | 2021/02/26 07:40 | Martin Klizan v Prajnesh Gunneswaran | 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 | Rafael Matos v Pedro Sakamoto | 3-6,1-6 |
| ATP Buenos Aires | 2021/02/28 14:00 | Pedro Sakamoto v Agustin Velotti | 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 Andrej Martin | 3-6,3-6 |