Round: 27 Ground: Hardcourt outdoor
| Challenger Pune | 2016/10/26 07:25 | Prajnesh Gunneswaran v N. Vijay Sundar Prashanth | 6-4,6-2 |
| ITF India F4 | 2015/09/17 06:00 | N. Vijay Sundar Prashanth v Prajnesh Gunneswaran | 6-3,6-2 |
| Challenger Kobe | 2016/11/08 03:40 | Prajnesh Gunneswaran v Laurent Lokoli | 3-6,6-7 |
| Challenger Canberra 2 | 2016/11/01 02:30 | Prajnesh Gunneswaran v Maverick Banes | 3-6,5-7 |
| Challenger Pune | 2016/10/29 09:50 | Sadio Doumbia v Prajnesh Gunneswaran | 4-6,6-4,6-3 |
| Challenger Pune | 2016/10/28 09:55 | Prajnesh Gunneswaran v Duckhee Lee | 6-2,7-5 |
| Challenger Pune | 2016/10/27 08:30 | Prajnesh Gunneswaran v Saketh Myneni | 6-7,6-2,6-0 |
| Challenger Pune | 2016/10/26 07:25 | Prajnesh Gunneswaran v N. Vijay Sundar Prashanth | 6-4,6-2 |
| Challenger Pune | 2016/10/24 08:20 | Prajnesh Gunneswaran v Haadin Bava | 7-5,2-6,6-4 |
| Challenger Ho Chi Minh City | 2016/10/12 04:55 | Prajnesh Gunneswaran v Go Soeda | 6-4,3-6,2-6 |
| Challenger Canberra 2 | 2016/11/03 03:15 | N. Vijay Sundar Prashanth v John-Patrick Smith | 1-6,2-6 |
| Challenger Canberra 2 | 2016/11/01 01:10 | Luke Saville v N. Vijay Sundar Prashanth | 4-6,2-6 |
| Challenger Pune | 2016/10/26 07:25 | Prajnesh Gunneswaran v N. Vijay Sundar Prashanth | 6-4,6-2 |
| Challenger Pune | 2016/10/25 05:30 | N. Vijay Sundar Prashanth v Jayesh Pungliya | 6-2,6-4 |
| Challenger Ho Chi Minh City | 2016/10/11 03:00 | N. Vijay Sundar Prashanth v Tatsuma Ito | 3-6,7-6,1-6 |
| Challenger Ho Chi Minh City Qual | 2016/10/10 04:20 | N.Sriram Balaji v N. Vijay Sundar Prashanth | 6-7,2-6 |
| Challenger Ho Chi Minh City Qual | 2016/10/09 10:55 | Masato Shiga v N. Vijay Sundar Prashanth | 2-6,0-6 |
| ITF India F6 | 2016/09/23 03:30 | N. Vijay Sundar Prashanth v Sanam Singh | 4-6,6-7 |