Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| 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 Leon | 2019/04/27 20:00 | Blaz Rola v James Ward | 6-7,6-3,7-6 |
| Challenger Leon | 2019/04/26 21:25 | James Ward v Marcelo Arevalo | 6-3,6-4 |
| Challenger Leon | 2019/04/25 17:00 | James Ward v Darian King | 6-1,6-4 |
| Challenger Leon | 2019/04/23 17:10 | James Ward v Baptiste Crepatte | 6-3,6-4 |
| Challenger Sarasota | 2019/04/17 16:20 | James Ward v Sebastian Korda | 4-6,7-6,1-6 |
| ATP Houston | 2019/04/06 19:00 | Santiago Giraldo v James Ward | 6-4,6-4 |
| Challenger Monterrey | 2019/04/03 02:15 | James Ward v Ante Pavic | 5-7,6-7 |
| Challenger Shenzhen | 2019/03/13 03:35 | Stefano Napolitano v James Ward | 6-4,7-5 |