Round: 28 Ground: Hardcourt outdoor
| ITF India F4 | 2016/09/07 08:40 | Prajnesh Gunneswaran v Dalwinder Singh | 6-1,6-1 |
| Australian Open 2017 WC | 2016/12/03 04:15 | Denis Istomin v Prajnesh Gunneswaran | 6-2,1-6,11-9 |
| Australian Open 2017 WC | 2016/12/02 05:00 | Francis Casey Alcantara v Prajnesh Gunneswaran | 4-6,1-6 |
| Australian Open 2017 WC | 2016/12/01 03:15 | Prajnesh Gunneswaran v Xiao Gong | 4-6,6-4,6-2 |
| Challenger Astana 2 | 2016/11/24 06:45 | Aleksandr Nedovyesov v Prajnesh Gunneswaran | 6-2,6-3 |
| Challenger Astana 2 | 2016/11/23 06:30 | Soonwoo Kwon v Prajnesh Gunneswaran | 3-6,6-4,1-6 |
| Challenger Astana 2 | 2016/11/22 10:40 | Prajnesh Gunneswaran v Andrey Golubev | 6-4,6-2 |
| 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 |
| ITF India F5 | 2016/09/12 04:45 | Dalwinder Singh v Suraj R Prabodh | 6-3,4-6,6-4 |
| ITF India F4 | 2016/09/07 08:40 | Prajnesh Gunneswaran v Dalwinder Singh | 6-1,6-1 |
| 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 |