Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Charlottesville | 2021/11/05 16:00 | Brayden Schnur v Prajnesh Gunneswaran | 7-5,6-3 |
| Challenger Charlottesville | 2021/11/03 21:00 | Inaki Montes-De La Torre v Prajnesh Gunneswaran | 1-6,5-7 |
| Challenger Charlottesville | 2021/11/01 20:50 | Prajnesh Gunneswaran v Taro Daniel | 6-7,7-6,6-2 |
| Challenger Columbus | 2021/09/23 15:00 | Prajnesh Gunneswaran v Mikael Torpegaard | 1-6,4-6 |
| Challenger Columbus | 2021/09/21 22:35 | Prajnesh Gunneswaran v Aleksandar Kovacevic | 3-6,6-3,7-5 |
| Davis Cup | 2021/09/18 12:55 | Patrik Niklas-Salminen v Prajnesh Gunneswaran | 3-6,5-7 |
| Davis Cup | 2021/09/17 14:50 | Otto Virtanen v Prajnesh Gunneswaran | 6-3,7-6 |
| Challenger Saint-Tropez | 2021/08/30 12:25 | Prajnesh Gunneswaran v Hugo Grenier | 5-7,3-6 |
| ITF M15 Cancun | 2021/09/29 17:35 | Alfredo Perez v Colin Markes | 6-2,7-5 |
| ITF M15 Cancun | 2021/09/28 14:00 | Gabriel Roveri Sidney v Colin Markes | 1-6,4-6 |
| ITF M15 Cancun | 2021/09/27 14:30 | Colin Markes v Austin Ansari | 4-6,4-6 |
| ITF M15 Cancun | 2021/09/26 17:00 | Diego Bustamante v Colin Markes | 1-6,0-6 |
| ITF M15 Cancun | 2021/09/22 15:55 | Colin Markes v Christian Langmo | 6-7,6-4,2-6 |
| ITF M15 Cancun | 2021/09/21 14:00 | Colin Markes v Nikolas Moceanu | 6-3,6-2 |
| ITF M15 Cancun | 2021/09/20 14:00 | Colin Markes v Lance A L Castelan | 6-2,6-1 |
| ITF M15 Cancun | 2021/09/19 14:00 | Colin Markes v Enzo Frances Tessari | 6-1,6-3 |