| Challenger Busan | 2019/05/06 07:00 | Di Wu v Roy Smith | 6-3,3-6,6-1 |
| Challenger Busan | 2019/05/07 05:00 | Go Soeda v Di Wu | 6-1,6-1 |
| Challenger Busan | 2019/05/06 07:00 | Di Wu v Roy Smith | 6-3,3-6,6-1 |
| Challenger Nanchang | 2019/04/23 06:35 | Di Wu v James Duckworth | 6-7,3-6 |
| Challenger Nanchang | 2019/04/22 05:55 | Di Wu v Jie Cui | 6-1,6-2 |
| Challenger Anning | 2019/04/15 09:25 | Di Wu v Max Purcell | 4-6,6-4,2-6 |
| Challenger Zhangjiagang | 2019/03/19 07:35 | Viktor Galovic v Di Wu | 6-1,6-4 |
| Challenger Zhangjiagang | 2019/03/18 05:40 | Xin Gao v Di Wu | 5-7,4-6 |
| Challenger Shenzhen | 2019/03/11 06:35 | Di Wu v Maverick Banes | 3-6,4-6 |
| Challenger Busan | 2019/05/06 07:00 | Di Wu v Roy Smith | 6-3,3-6,6-1 |
| Challenger Monterrey | 2019/04/01 22:45 | Roy Smith v Janko Tipsarevic | 6-7,4-6 |
| Challenger Drummondville | 2019/03/11 18:45 | Michael Redlicki v Roy Smith | 6-1,6-1 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Roy Smith | 6-3,6-3 |
| ATP New York | 2019/02/10 21:20 | Ramkumar Ramanathan v Roy Smith | 4-6,6-2,6-4 |
| Challenger Cleveland | 2019/01/30 02:55 | Roy Smith v Donald Young | 6-4,0-6,7-6 |
| Challenger Cleveland | 2019/01/28 18:25 | Roy Smith v Gijs Brouwer | 7-6,6-3 |
| Challenger Newport Beach | 2019/01/21 19:30 | Roy Smith v Benjamin Bonzi | 2-6,5-7 |