Stadium: Center Court Round: 28 Ground: Hardcourt outdoor
| Challenger - Chennai | 2019/02/08 08:05 | Gunneswaran, Prajnesh v James Duckworth | 6-4,6-3 |
| Challenger - Chennai | 2019/02/07 08:00 | Gunneswaran, Prajnesh v Arjun Kadhe | 6-4,6-2 |
| Challenger - Chennai | 2019/02/06 07:20 | Gunneswaran, Prajnesh v Daniel Altmaier | 6-4,6-4 |
| Coupe Davis | 2019/02/02 06:30 | Gunneswaran, Prajnesh v Seppi, Andreas | 1-6,4-6 |
| Coupe Davis | 2019/02/01 07:00 | Gunneswaran, Prajnesh v Matteo Berrettini | 4-6,3-6 |
| Open d'Australie | 2019/01/14 01:25 | Frances Tiafoe v Gunneswaran, Prajnesh | 7-6,6-3,6-3 |
| Open d'Australie | 2019/01/11 00:40 | Gunneswaran, Prajnesh v Yosuke Watanuki | 6-7,6-4,6-4 |
| Open d'Australie | 2019/01/10 03:40 | Gunneswaran, Prajnesh v Lopez Perez | 6-3,6-3 |
| Challenger - Chennai | 2019/02/08 08:15 | Harris, Andrew v Alejandro Davidovich Fokina | 1-6,7-6,6-2 |
| Challenger - Chennai | 2019/02/07 05:00 | Gianluca Mager v Harris, Andrew | 6-7,6-7 |
| Challenger - Chennai | 2019/02/05 07:30 | Harris, Andrew v Yang, Tsung-Hua | 6-2,6-1 |
| Challenger - Chennai | 2019/02/04 08:25 | Harris, Andrew v Aleksandar Vukic | 6-4,6-4 |
| Challenger Launceston | 2019/01/29 04:25 | Harris, Andrew v Sela, Dudi | 3-6,2-6 |
| Challenger Launceston | 2019/01/28 03:20 | Harris, Andrew v Rinky Hijikata | 1-6,7-6,6-3 |
| Challenger - Burnie | 2019/01/21 05:30 | Li, Zhe v Harris, Andrew | 7-5,6-7,6-3 |
| Challenger Canberra | 2019/01/08 23:00 | Harris, Andrew v Elliot Benchetrit | 6-7,6-7 |