| Challenger Bangkok 4 | 2016/08/30 09:40 | Duckhee Lee v Prajnesh Gunneswaran | 4-6,0-6 |
| Challenger Bastad | 2016/07/04 09:40 | Andrey Rublev v Prajnesh Gunneswaran | 6-7,7-5,7-6 |
| Challenger Bastad Qual | 2016/07/03 11:25 | Prajnesh Gunneswaran v Fred Simonsson | 4-6,7-5,6-3 |
| Challenger Bastad Qual | 2016/07/02 12:20 | Prajnesh Gunneswaran v Jonathan Mridha | 7-5,6-4 |
| Challenger Marburg Qual | 2016/06/27 10:00 | Sumit Nagal v Prajnesh Gunneswaran | 6-3,6-3 |
| Challenger Marburg Qual | 2016/06/26 14:10 | Sergey Betov v Prajnesh Gunneswaran | 2-6,4-6 |
| Challenger Marburg Qual | 2016/06/26 08:00 | Prajnesh Gunneswaran v Alexey Vatutin | 6-2,6-3 |
| ITF France F6 | 2016/03/16 13:40 | Maxime Authom v Prajnesh Gunneswaran | 6-2,6-2 |
| Challenger Bangkok 4 | 2016/08/30 09:50 | Edan Leshem v Sergey Betov | 6-3,3-6,6-1 |
| ITF Canada F5 | 2016/07/09 19:40 | Edan Leshem v Peter Polansky | 4-6,7-5,1-6 |
| ITF Canada F5 | 2016/07/08 17:00 | Alexios Halebian v Edan Leshem | 3-6,1-6 |
| ITF Canada F5 | 2016/07/07 17:00 | Tim Kopinski v Edan Leshem | 2-6,3-6 |
| ITF Canada F5 | 2016/07/06 22:20 | Patrick Davidson v Edan Leshem | 1-6,0-6 |
| ITF Canada F4 | 2016/06/30 17:00 | Edan Leshem v Alexios Halebian | 1-6,6-3,4-6 |
| ITF Canada F3 | 2016/06/23 18:10 | Edan Leshem v Raymond Sarmiento | 3-6,0-6 |
| ITF Canada F3 | 2016/06/21 17:00 | Edan Leshem v Nicholas Reyes | 6-4,6-3 |