Stadium: Mercedes Court Round: 64 Ground: Grass
| ATP Munich | 2019/04/28 11:30 | Prajnesh Gunneswaran v Denis Istomin | 6-4,2-6,2-6 |
| ATP Munich | 2019/04/27 14:00 | Prajnesh Gunneswaran v Alexander Erler | 3-6,7-6,7-5 |
| Challenger Anning | 2019/04/21 06:00 | Jay Clarke v Prajnesh Gunneswaran | 6-4,6-3 |
| Challenger Anning | 2019/04/20 04:00 | Kamil Majchrzak v Prajnesh Gunneswaran | 6-7,7-6,4-6 |
| Challenger Anning | 2019/04/19 05:30 | Nikola Milojevic v Prajnesh Gunneswaran | 5-7,3-6 |
| Challenger Anning | 2019/04/18 05:50 | Adam Pavlasek v Prajnesh Gunneswaran | 5-7,3-6 |
| Challenger Anning | 2019/04/16 07:10 | Saketh Myneni v Prajnesh Gunneswaran | 2-6,4-6 |
| ATP Miami | 2019/03/21 21:15 | Jaume Munar v Prajnesh Gunneswaran | 7-6,6-4 |
| Challenger Ostrava | 2019/05/01 11:40 | Matteo Viola v Ivan Gakhov | 4-6,4-6 |
| Challenger Francavilla | 2019/04/23 12:00 | Matteo Viola v Mikael Ymer | 1-6,2-6 |
| Challenger Francavilla | 2019/04/22 11:20 | Matteo Viola v Carlos Boluda-Purkiss | 6-3,6-2 |
| Challenger Anning | 2019/04/17 06:00 | Matteo Viola v Jay Clarke | 4-6,3-6 |
| Challenger Anning | 2019/04/15 10:10 | Xin Gao v Matteo Viola | 3-6,1-6 |
| Challenger Sophia Antipolis | 2019/04/01 14:55 | Matteo Viola v Johan Sebastien Tatlot | 2-6,3-6 |
| Challenger St Brieuc | 2019/03/28 19:20 | Gregoire Barrere v Matteo Viola | 6-1,6-1 |
| Challenger St Brieuc | 2019/03/27 12:30 | Matteo Viola v Daniel Brands | 6-3,7-6 |