Round: 26 Ground: Clay
| ITF India F4 | 2016/09/06 11:55 | Prajnesh Gunneswaran v Irfan Hussain | 6-0,6-2 |
| 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 |
| ITF India F4 | 2016/09/06 04:30 | Aryan Goveas v Dalwinder Singh | 4-6,3-6 |
| ITF Zimbabwe F3 | 2016/07/04 09:30 | Dalwinder Singh v Tucker Vorster | 2-6,2-6 |
| ITF Zimbabwe F2 | 2016/06/28 11:40 | Lloyd Harris v Dalwinder Singh | 6-3,6-3 |
| ITF Zimbabwe F1 | 2016/06/22 09:40 | Lloyd Harris v Dalwinder Singh | 6-1,6-2 |
| ITF Zimbabwe F1 | 2016/06/21 10:05 | Michael-Ray Pallares-Gonzalez v Dalwinder Singh | 6-7,6-7 |
| ITF India F3 | 2016/05/14 09:30 | Vishnu Vardhan v Dalwinder Singh | 7-6,6-4 |
| ITF India F3 | 2016/05/13 09:30 | Dalwinder Singh v Vijayant Malik | 6-4,4-6,6-4 |
| ITF India F3 | 2016/05/12 10:00 | Yuya Ito v Dalwinder Singh | 4-6,6-0,6-7 |