Stadium: Mercedes Court Round: 64 Ground: Grass
| 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 Budapest | 2019/02/04 18:55 | Pavel Kotov v Matteo Viola | 1-6,6-4,6-3 |
| Challenger Da Nang | 2019/01/12 04:30 | Marcel Granollers v Matteo Viola | 6-2,6-0 |
| Challenger Da Nang | 2019/01/11 06:00 | Thai-Son Kwiatkowski v Matteo Viola | 7-5,6-7,2-6 |
| Challenger Da Nang | 2019/01/10 05:00 | Yan Bai v Matteo Viola | 3-6,6-7 |
| Challenger Da Nang | 2019/01/09 07:30 | Benjamin Hassan v Matteo Viola | 4-6,1-6 |
| Challenger Da Nang | 2019/01/07 08:00 | Wishaya Trongcharoenchaikul v Matteo Viola | 6-4,3-6,4-6 |
| Challenger Andria | 2018/11/20 17:45 | Matteo Viola v Sergiy Stakhovsky | 1-6,5-7 |
| Challenger Bratislava | 2018/11/04 12:20 | Matteo Viola v Johannes Haerteis | 3-6,6-7 |