Stadium: Court 8 Round: 28 Ground: Hardcourt outdoor
| ITF M15 Cancun | 2019/07/19 13:30 | Jack Draper v Christian Langmo | 7-5,6-3 |
| ITF M15 Cancun | 2019/07/16 13:30 | Jack Draper v Peter Bertran | 6-1,6-2 |
| ITF M15 Cancun | 2019/07/12 13:30 | Jack Draper v Aron Pierce | 6-3,6-3 |
| 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 |
| ITF M15 Cancun | 2019/07/19 13:30 | Felix Corwin v Justin Roberts | 6-7,6-2,3-6 |
| ITF M15 Cancun | 2019/07/18 15:00 | Justin Roberts v Gage Brymer | 7-6,6-7,6-3 |
| ITF M15 Cancun | 2019/07/17 13:30 | Riaan Du Toit v Justin Roberts | 1-6,2-6 |
| ITF M15 Cancun | 2019/07/15 19:00 | Justin Roberts v Ricardo David Mayagoitia | 6-1,6-0 |
| ITF M15 Cancun | 2019/07/09 16:05 | Nicolas Moreno De Alboran v Justin Roberts | 5-7,7-6,7-5 |
| ITF M15 Cancun | 2019/07/05 13:30 | Justin Roberts v Nicolas Mejia | 4-6,5-7 |
| ITF M15 Cancun | 2019/07/04 17:30 | Gage Brymer v Justin Roberts | 2-6,3-6 |
| ITF M15 Cancun | 2019/07/02 13:30 | Justin Roberts v Isaac Stoute | 7-5,6-4 |