Stadium: Court 5 Round: 24 Ground: Hardcourt outdoor
| Challenger - Nottingham | 2019/06/11 18:40 | Jack Draper v Yunseong Chung | 5-7,6-0,6-2 |
| Challenger - Helsingi | 2019/11/12 13:25 | Elias Ymer v Jack Draper | 6-3,3-6,6-4 |
| Challenger - Helsingi | 2019/11/11 13:50 | Jonas Forejtek v Jack Draper | 6-3,3-6,4-6 |
| ITF M25 Fort Worth | 2019/10/24 18:05 | Nathan Ponwith v Jack Draper | 6-3,6-4 |
| ITF M25 Fort Worth | 2019/10/23 15:00 | Tyler Zink v Jack Draper | 2-6,1-6 |
| Challenger Las Vegas | 2019/10/14 19:35 | Jack Draper v Ryan Peniston | 5-7,6-7 |
| Challenger - Fairfield | 2019/10/11 21:40 | Christopher O'Connell v Jack Draper | 6-2,6-3 |
| Challenger - Fairfield | 2019/10/11 02:00 | Jack Draper v Donald Young | 6-3,7-6 |
| Challenger - Fairfield | 2019/10/10 02:30 | Jack Sock v Jack Draper | 6-3,6-7,3-6 |
| Australian Open WC | 2019/12/07 05:30 | Yunseong Chung v Tatsuma Ito | 6-1,4-6,4-6 |
| Australian Open WC | 2019/12/06 06:00 | Mukund Sasikumar v Yunseong Chung | 4-6,3-6 |
| Australian Open WC | 2019/12/04 04:00 | Yunseong Chung v Denis Istomin | 7-5,6-3 |
| Challenger Kobe | 2019/11/05 05:35 | Yunseong Chung v Yuichi Sugita | 1-6,4-6 |
| Challenger Kobe | 2019/11/04 04:00 | Yunseong Chung v Yusuke Takahashi | 7-6,7-6 |
| Challenger Shenzhen 2 | 2019/10/29 02:00 | Yunseong Chung v Jonas Forejtek | 4-6,3-6 |
| Challenger Liuzhou | 2019/10/23 02:00 | Yunseong Chung v Alejandro Davidovich Fokina | 5-7,5-7 |
| Challenger Liuzhou | 2019/10/21 06:00 | Yunseong Chung v Takuto Niki | 6-2,7-6 |