Stadium: Stadium Round: 28 Ground: Hardcourt outdoor
| Challenger Little Rock | 2019/06/08 16:35 | Duckhee Lee v Mitchell Krueger | 4-6,6-3,6-1 |
| Challenger Little Rock | 2019/06/07 21:00 | Zhizhen Zhang v Duckhee Lee | 4-6,7-6,6-7 |
| Challenger Little Rock | 2019/06/05 15:00 | Jordi Arconada v Duckhee Lee | 1-6,4-6 |
| Challenger Gwangju | 2019/05/15 03:40 | Duckhee Lee v Yunseong Chung | 4-6,2-6 |
| Challenger Busan | 2019/05/09 04:40 | Ricardas Berankis v Duckhee Lee | 6-3,3-6,6-3 |
| Challenger Busan | 2019/05/08 04:50 | Duckhee Lee v Yuichi Sugita | 5-7,6-3,7-6 |
| Challenger Busan | 2019/05/07 06:20 | Makoto Ochi v Duckhee Lee | 6-7,4-6 |
| Challenger Seoul | 2019/04/30 03:35 | Ji Sung Nam v Duckhee Lee | 7-5,6-1 |
| Challenger Little Rock | 2019/06/08 16:10 | Darian King v Raymond Sarmiento | 6-3,6-7,7-5 |
| Challenger Little Rock | 2019/06/07 23:10 | Darian King v Zhe Li | 7-6,6-3 |
| Challenger Little Rock | 2019/06/05 18:40 | Darian King v Oliver Crawford | 6-4,6-4 |
| French Open | 2019/05/20 08:00 | Peter Polansky v Darian King | 6-4,6-4 |
| Challenger Puerto Vallarta | 2019/05/04 00:00 | Darian King v Alejandro Tabilo | 1-6,7-5,5-7 |
| Challenger Puerto Vallarta | 2019/05/03 02:45 | Joao Menezes v Darian King | 5-7,5-7 |
| Challenger Puerto Vallarta | 2019/05/01 17:00 | Andres Artunedo Martinavarr v Darian King | 4-6,4-6 |
| Challenger Leon | 2019/04/25 17:00 | James Ward v Darian King | 6-1,6-4 |