Stadium: Court 3 Round: 24 Ground: Hardcourt outdoor
| Challenger - Busan | 2019/05/06 07:00 | Wu, Di v Smith, Roy | 6-3,3-6,6-1 |
| Challenger - Busan | 2019/05/07 05:00 | Soeda, Go v Wu, Di | 6-1,6-1 |
| Challenger - Busan | 2019/05/06 07:00 | Wu, Di v Smith, Roy | 6-3,3-6,6-1 |
| Nanchang, China | 2019/04/23 06:35 | Wu, Di v James Duckworth | 6-7,3-6 |
| Nanchang, China | 2019/04/22 05:55 | Wu, Di v Jie Cui | 6-1,6-2 |
| Anning, China | 2019/04/15 09:25 | Wu, Di v Max Purcell | 4-6,6-4,2-6 |
| Zhangjiagang, China | 2019/03/19 07:35 | Galovic, Viktor v Wu, Di | 6-1,6-4 |
| Zhangjiagang, China | 2019/03/18 05:40 | Gao, Xin v Wu, Di | 5-7,4-6 |
| Challenger - Shenzhen | 2019/03/11 06:35 | Wu, Di v Banes, Maverick | 3-6,4-6 |
| Challenger - Busan | 2019/05/06 07:00 | Wu, Di v Smith, Roy | 6-3,3-6,6-1 |
| Monterrey, Mexico | 2019/04/01 22:45 | Smith, Roy v Tipsarevic, Janko | 6-7,4-6 |
| Drummondville, Canada | 2019/03/11 18:45 | Redlicki, Michael v Smith, Roy | 6-1,6-1 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Smith, Roy | 6-3,6-3 |
| New York, USA | 2019/02/10 21:20 | Ramkumar Ramanathan v Smith, Roy | 4-6,6-2,6-4 |
| Challenger - Cleveland | 2019/01/30 02:55 | Smith, Roy v Young, Donald | 6-4,0-6,7-6 |
| Challenger - Cleveland | 2019/01/28 18:25 | Smith, Roy v Gijs Brouwer | 7-6,6-3 |
| Newport Beach, USA | 2019/01/21 19:30 | Smith, Roy v Benjamin Bonzi | 2-6,5-7 |