Stadium: Centre Court Round: 26 Ground: Hardcourt outdoor
| Challenger Shanghai | 2019/09/10 05:50 | Prajnesh Gunneswaran v James Ward | 6-4,7-6 |
| 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 |
| Challenger Shanghai | 2019/09/11 02:30 | Tak Khunn Wang v Goncalo Oliveira | 7-6,3-6,4-6 |
| Challenger Jinan | 2019/09/02 07:40 | Igor Sijsling v Goncalo Oliveira | 3-6,2-6 |
| Challenger Baotou | 2019/08/29 05:35 | Aleksandar Vukic v Goncalo Oliveira | 4-6,6-3,0-6 |
| Challenger Baotou | 2019/08/28 05:55 | Luca Castelnuovo v Goncalo Oliveira | 4-6,4-6 |
| Challenger Manerbio | 2019/08/07 08:00 | Goncalo Oliveira v Andrea Pellegrino | 1-6,4-6 |
| Challenger Chengdu | 2019/08/01 07:45 | Goncalo Oliveira v Shuichi Sekiguchi | 4-6,6-3,4-6 |
| Challenger Chengdu | 2019/07/31 07:00 | Goncalo Oliveira v Arjun Kadhe | 7-6,6-3 |
| Challenger Tampere | 2019/07/24 07:30 | Jeroen Vanneste v Goncalo Oliveira | 6-3,7-6 |