Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| 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 M25 Abuja | 2019/04/17 09:00 | Simon Yitbarek v Jack Draper | 3-6,4-6 |
| ITF M25 Bakersfield | 2019/03/12 21:15 | Alen Avidzba v Jack Draper | 4-6,3-6 |
| ITF M15 Cancun | 2019/07/08 13:30 | Kalman Boyd v Christopher Rosensteel | 6-2,6-2 |
| ITF M15 Cancun | 2019/06/13 13:30 | Kalman Boyd v Alejandro Mendoza | 3-6,0-6 |
| ITF M15 Cancun | 2019/06/12 13:30 | Ivar Jose Aramburu Contreras v Kalman Boyd | 1-6,4-6 |
| ITF M15 Cancun | 2019/06/10 19:00 | Sebastian Eguez v Kalman Boyd | 3-6,1-6 |
| ITF M15 Cancun | 2019/06/10 14:30 | Kalman Boyd v Razvan Baiant | 6-1,6-1 |
| ITF M15 Cancun | 2019/06/03 16:00 | Alex Hernandez v Kalman Boyd | 6-2,6-7,10-8 |
| ITF M15 Cancun | 2019/06/03 13:30 | Kalman Boyd v Tomislav E Papac | 6-1,6-2 |
| ITF USA F23 Qual | 2017/07/02 17:30 | Christopher G Haworth v Kalman Boyd | 6-2,6-2 |