Stadium: Central Round: 28 Ground: Hardcourt outdoor
| Challenger Newport Beach | 2019/01/25 19:00 | Enzo Couacaud v Darian King | 6-3,3-6,7-6 |
| Challenger Gatineau | 2019/07/19 15:00 | Darian King v Maxime Janvier | 6-3,1-6,6-1 |
| Challenger Gatineau | 2019/07/18 17:40 | Yasutaka Uchiyama v Darian King | 6-4,2-6,3-6 |
| Challenger Gatineau | 2019/07/17 17:05 | Liam Draxl v Darian King | 6-3,5-7,2-6 |
| Challenger Winnipeg | 2019/07/11 21:00 | Maxime Cressy v Darian King | 7-5,7-6 |
| Challenger Winnipeg | 2019/07/10 16:55 | Brydan Klein v Darian King | 0-6,6-7 |
| Wimbledon | 2019/06/24 10:00 | Darian King v Sergiy Stakhovsky | 3-6,2-6 |
| Challenger Little Rock | 2019/06/08 21:00 | Duckhee Lee v Darian King | 6-0,6-0 |
| Challenger Little Rock | 2019/06/08 16:10 | Darian King v Raymond Sarmiento | 6-3,6-7,7-5 |
| Challenger Gatineau | 2019/07/19 15:00 | Marc Polmans v Enzo Couacaud | 1-6,4-6 |
| Challenger Gatineau | 2019/07/18 15:25 | Enzo Couacaud v Soonwoo Kwon | 7-5,7-5 |
| Challenger Gatineau | 2019/07/16 20:45 | Enzo Couacaud v Carlos Gomez-Herrera | 6-2,6-3 |
| Challenger Winnipeg | 2019/07/11 16:00 | Daniel Nguyen v Enzo Couacaud | 1-6,6-3,6-2 |
| Challenger Winnipeg | 2019/07/10 20:05 | Toshihide Matsui v Enzo Couacaud | 3-6,2-6 |
| Wimbledon | 2019/06/27 10:00 | Kamil Majchrzak v Enzo Couacaud | 6-2,6-4,6-0 |
| Wimbledon | 2019/06/26 10:00 | Enzo Couacaud v Gianluca Mager | 6-3,6-4 |
| Wimbledon | 2019/06/24 11:00 | Enzo Couacaud v Sebastian Ofner | 3-6,6-3,6-1 |