Stadium: Center Court Round: 28 Ground: Hardcourt outdoor
| 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 |
| Australian Open | 2019/01/10 03:40 | Prajnesh Gunneswaran v Enrique Lopez-Perez | 6-3,6-3 |
| Challenger Chennai | 2019/02/08 08:15 | Andrew Harris v Alejandro Davidovich Fokina | 1-6,7-6,6-2 |
| Challenger Chennai | 2019/02/07 05:00 | Gianluca Mager v Andrew Harris | 6-7,6-7 |
| Challenger Chennai | 2019/02/05 07:30 | Andrew Harris v Tsung-Hua Yang | 6-2,6-1 |
| Challenger Chennai | 2019/02/04 08:25 | Andrew Harris v Aleksandar Vukic | 6-4,6-4 |
| Challenger Launceston | 2019/01/29 04:25 | Andrew Harris v Dudi Sela | 3-6,2-6 |
| Challenger Launceston | 2019/01/28 03:20 | Andrew Harris v Rinky Hijikata | 1-6,7-6,6-3 |
| Challenger Burnie | 2019/01/21 05:30 | Zhe Li v Andrew Harris | 7-5,6-7,6-3 |
| Challenger Canberra | 2019/01/08 23:00 | Andrew Harris v Elliot Benchetrit | 6-7,6-7 |