Stadium: Cancha 1 Round: 26 Ground: Hardcourt outdoor
| 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 |
| ATP Dubai | 2019/02/23 09:40 | Jiri Vesely v James Ward | 7-6,7-6 |
| ATP New York | 2019/02/10 22:25 | Alexei Popyrin v James Ward | 7-5,6-4 |
| ATP Sofia | 2019/02/03 11:40 | Stefano Travaglia v James Ward | 3-6,6-4,7-6 |
| Challenger Leon | 2019/04/23 17:55 | Skander Mansouri v Darian King | 3-6,2-6 |
| ATP Houston | 2019/04/08 18:00 | Darian King v Pedja Krstin | 6-7,5-7 |
| ATP Houston | 2019/04/06 19:55 | Peter Polansky v Darian King | 4-6,1-6 |
| Challenger Monterrey | 2019/04/04 18:35 | Tennys Sandgren v Darian King | 7-6,4-6,6-2 |
| Challenger Monterrey | 2019/04/02 19:45 | Evan King v Darian King | 6-4,6-7,1-6 |
| ATP Miami | 2019/03/18 14:00 | Darian King v Denis Istomin | 4-6,6-3,6-7 |
| ATP Indian Wells | 2019/03/06 02:10 | Darian King v Elias Ymer | 6-1,1-6,2-6 |
| Challenger Indian Wells | 2019/02/26 00:20 | Darian King v Kamil Majchrzak | 4-6,3-6 |