Stadium: Court 6 Round: 27 Ground: Hardcourt outdoor
| ITF - M15 Cancun | 2019/07/11 13:30 | Jack Draper v Peter Bertran | 6-1,6-3 |
| ITF - M15 Cancun | 2019/07/10 16:25 | Jack Draper v Kalman Boyd | 6-1,6-4 |
| Wimbledon | 2019/06/24 14:20 | Jack Draper v Yasutaka Uchiyama | 4-6,6-7 |
| ATP - Queens | 2019/06/15 10:00 | Alexander Bublik v Jack Draper | 6-2,1-6,6-3 |
| Challenger - Nottingham | 2019/06/13 13:30 | Daniel Evans v Jack Draper | 7-5,6-3 |
| Challenger - Nottingham | 2019/06/11 18:40 | Jack Draper v Yunseong Chung | 5-7,6-0,6-2 |
| ITF M25 Abuja | 2019/04/24 10:25 | Maxime Mora v Jack Draper | 0-6,0-6 |
| ITF M25 Abuja | 2019/04/18 10:25 | Danylo Kalenichenko v Jack Draper | 6-4,7-5 |
| ITF - M15 Cancun | 2019/07/11 16:20 | Aron Pierce v Ben Jones | 6-3,6-4 |
| ITF - M15 Cancun | 2019/07/10 13:30 | Aron Pierce v Joaquin Marquez | 7-5,6-4 |
| ITF - M15 Cancun | 2019/07/08 18:30 | Aron Pierce v Jack Gibbens | 6-2,6-3 |
| ITF - M15 Cancun | 2019/07/08 14:30 | Aron Pierce v Zakai Stone | 6-1,6-0 |
| ITF - M15 Cancun | 2019/07/03 15:30 | Juan A H Serrano v Aron Pierce | 6-1,6-4 |
| ITF - M15 Cancun | 2019/07/01 18:30 | Aron Pierce v Andreas A Lavdas | 6-1,6-2 |
| ITF - M15 Cancun | 2019/07/01 13:30 | Aron Pierce v Nikolay Sysoev | 6-1,6-1 |
| ITF - M15 Cancun | 2019/06/11 13:30 | Aron Pierce v Jorge Panta | 2-6,5-7 |