Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
| Challenger Bangkok | 2019/02/12 04:30 | Prajnesh Gunneswaran v JC Aragone | 3-6,1-6 |
| 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 |
| Challenger Bangkok 1A | 2019/02/19 03:00 | Denis Yevseyev v Yan Bai | 7-5,6-4 |
| Challenger Bangkok | 2019/02/13 04:40 | Denis Yevseyev v Tobias Kamke | 5-7,1-6 |
| Challenger Bangkok | 2019/02/11 04:30 | Denis Yevseyev v Calvin Hemery | 6-2,6-2 |
| Challenger Da Nang | 2019/01/10 06:45 | Denis Yevseyev v Gerard Granollers-Pujol | 6-4,6-7,6-3 |
| Challenger Da Nang | 2019/01/09 07:10 | Mukund Sasikumar v Denis Yevseyev | 4-6,2-6 |
| Challenger Da Nang | 2019/01/07 06:15 | Arjun Kadhe v Denis Yevseyev | 2-6,1-6 |
| ITF M25 Hong Kong | 2019/01/03 07:15 | Evan Furness v Denis Yevseyev | 6-7,6-0,6-3 |
| ITF M25 Hong Kong | 2019/01/02 09:45 | Jordi Samper-Montana v Denis Yevseyev | 4-6,3-6 |