Round: 25 Ground: Clay
| Challenger Bangkok 4 | 2016/09/01 04:00 | Prajnesh Gunneswaran v Edan Leshem | 6-4,3-6,5-7 |
| 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 India F4 | 2015/03/21 04:00 | Aditya Deswal v Irfan Hussain | 4-6,3-6 |