Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ATP Queen's | 2019/06/15 11:40 | James Ward v Prajnesh Gunneswaran | 6-1,6-4 |
| Challenger Jinan | 2019/09/06 06:55 | Prajnesh Gunneswaran v Go Soeda | 6-7,6-3,3-6 |
| Challenger Jinan | 2019/09/05 07:05 | Prajnesh Gunneswaran v Tung-Lin Wu | 6-4,7-6 |
| Challenger Jinan | 2019/09/04 06:00 | Prajnesh Gunneswaran v Renta Tokuda | 6-2,6-2 |
| US Open | 2019/08/26 17:05 | Prajnesh Gunneswaran v Daniil Medvedev | 4-6,1-6,2-6 |
| ATP Winston-Salem | 2019/08/20 18:25 | Benoit Paire v Prajnesh Gunneswaran | 6-3,7-5 |
| ATP Winston-Salem | 2019/08/18 21:15 | Prajnesh Gunneswaran v Cedrik-Marcel Stebe | 6-3,6-4 |
| ATP Los Cabos | 2019/08/01 01:50 | Prajnesh Gunneswaran v Taylor Fritz | 6-4,3-6,2-6 |
| ATP Los Cabos | 2019/07/30 00:00 | Prajnesh Gunneswaran v John Millman | 6-4,1-6,6-2 |
| Challenger Šanghaj | 2019/09/09 02:00 | James Ward v Renta Tokuda | 6-3,6-4 |
| Challenger Jinan | 2019/09/05 03:00 | Enrique Lopez-Perez v James Ward | 7-6,6-3 |
| Challenger Jinan | 2019/09/03 04:45 | James Ward v Yasutaka Uchiyama | 4-6,7-6,6-0 |
| Challenger Jinan | 2019/09/02 06:20 | Aleksandar Vukic v James Ward | 3-6,6-3,3-6 |
| US Open | 2019/08/22 17:35 | James Ward v Marco Trungelliti | 4-6,3-6 |
| US Open | 2019/08/20 21:05 | James Ward v Zhe Li | 7-6,6-3 |
| Challenger Vancouver | 2019/08/13 00:05 | Enzo Couacaud v James Ward | 1-6,6-4,6-3 |
| Challenger Aptos | 2019/08/05 17:00 | James Ward v Zhe Li | 4-6,2-6 |