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 Antalya | 2019/06/25 12:30 | Lorenzo Sonego v Prajnesh Gunneswaran | 6-7,6-0,7-5 |
| ATP Antalya | 2019/06/24 10:30 | Prajnesh Gunneswaran v Janko Tipsarevic | 6-0,7-6 |
| 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 |
| ATP Eastbourne | 2019/06/25 12:30 | James Ward v Thomas Fabbiano | 6-2,3-6,1-6 |
| ATP Eastbourne | 2019/06/23 12:10 | Denis Kudla v James Ward | 3-6,2-6 |
| ATP Eastbourne | 2019/06/22 14:20 | James Ward v Lloyd Harris | 4-6,7-6,6-4 |
| 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 |