Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ATP Queens | 2019/06/15 11:40 | James Ward v Prajnesh Gunneswaran | 6-1,6-4 |
| ATP Queens | 2019/06/15 11:40 | James Ward v Prajnesh Gunneswaran | 6-1,6-4 |
| 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 |
| ATP Queens | 2019/06/17 16:55 | Gilles Simon v James Ward | 3-6,6-3,7-6 |
| ATP Queens | 2019/06/16 11:40 | Ivo Karlovic v James Ward | 6-7,4-6 |
| ATP Queens | 2019/06/15 11:40 | James Ward v Prajnesh Gunneswaran | 6-1,6-4 |
| Challenger Nottingham | 2019/06/11 13:25 | Stefano Napolitano v James Ward | 7-5,7-6 |
| Challenger Surbiton | 2019/06/06 14:55 | James Ward v Denis Kudla | 3-6,6-4,3-6 |
| Challenger Surbiton | 2019/06/05 14:30 | Sergiy Stakhovsky v James Ward | 7-6,3-6,4-6 |
| Challenger Surbiton | 2019/06/03 13:30 | Paul Jubb v James Ward | 5-7,6-4,3-6 |
| French Open | 2019/05/20 15:00 | James Ward v Oscar Otte | 1-6,2-6 |