Stadium: Mercedes Court Round: 64 Ground: Grass
| French Open | 2019/05/26 13:10 | Prajnesh Gunneswaran v Hugo Dellien | 1-6,3-6,1-6 |
| 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 |
| Challenger Vicenza | 2019/05/30 07:30 | Matteo Viola v Mats Moraing | 4-6,1-6 |
| French Open | 2019/05/21 08:00 | Mathias Bourgue v Matteo Viola | 4-6,6-1,6-3 |
| Challenger Heilbronn | 2019/05/14 11:20 | Matteo Viola v Attila Balazs | 4-6,3-6 |
| Challenger Rome | 2019/05/09 08:00 | Matteo Viola v Henri Laaksonen | 4-6,3-6 |
| Challenger Rome | 2019/05/07 08:00 | Matteo Viola v Renzo Olivo | 6-3,7-5 |
| 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 |