Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| Challenger Aptos | 2018/08/08 22:55 | JC Aragone v Prajnesh Gunneswaran | 6-4,5-7,4-6 |
| Challenger Chennai | 2019/02/09 07:30 | Prajnesh Gunneswaran v Andrew Harris | 4-6,6-3,0-6 |
| Challenger Chennai | 2019/02/08 08:05 | Prajnesh Gunneswaran v James Duckworth | 6-4,6-3 |
| Challenger Chennai | 2019/02/07 08:00 | Prajnesh Gunneswaran v Arjun Kadhe | 6-4,6-2 |
| Challenger Chennai | 2019/02/06 07:20 | Prajnesh Gunneswaran v Daniel Altmaier | 6-4,6-4 |
| Davis Cup | 2019/02/02 06:30 | Prajnesh Gunneswaran v Andreas Seppi | 1-6,4-6 |
| Davis Cup | 2019/02/01 07:00 | Prajnesh Gunneswaran v Matteo Berrettini | 4-6,3-6 |
| Australian Open | 2019/01/14 01:25 | Frances Tiafoe v Prajnesh Gunneswaran | 7-6,6-3,6-3 |
| Australian Open | 2019/01/11 00:40 | Prajnesh Gunneswaran v Yosuke Watanuki | 6-7,6-4,6-4 |
| Challenger Bangkok | 2019/02/11 05:50 | JC Aragone v Gastao Elias | 6-4,6-2 |
| Challenger Newport Beach | 2019/01/24 20:40 | JC Aragone v Donald Young | 3-6,4-6 |
| Challenger Newport Beach | 2019/01/22 18:00 | Bjorn Fratangelo v JC Aragone | 5-7,4-6 |
| Challenger Newport Beach | 2019/01/21 18:00 | Ulises Blanch v JC Aragone | 6-7,6-2,4-6 |
| Australian Open | 2019/01/08 02:40 | JC Aragone v Maxime Janvier | 7-5,0-6,4-6 |
| Challenger Orlando | 2019/01/02 16:20 | Michael Redlicki v JC Aragone | 1-6,6-4,6-3 |
| Challenger Champaign | 2018/11/13 18:45 | Tak Khunn Wang v JC Aragone | 6-3,6-1 |
| Challenger Knoxville | 2018/11/06 20:50 | JC Aragone v Bradley Klahn | 2-6,6-7 |