Stadium: Chris Cammisa Court Round: 26 Ground: Hardcourt outdoor
| Challenger Fairfield | 2019/10/10 02:30 | Sock, Jack v Jack Draper | 6-3,6-7,3-6 |
| Challenger Fairfield | 2019/10/08 17:00 | Jack Draper v Alex Rybakov | 6-1,2-6,7-5 |
| ITF M25 Shrewsbury | 2019/09/28 13:00 | Jack Draper v Ocleppo, Julian | 6-4,6-0 |
| ITF M25 Shrewsbury | 2019/09/26 11:35 | Jack Draper v Vilardo, Francesco | 6-4,7-6 |
| ITF M25 Shrewsbury | 2019/09/25 11:45 | Jack Draper v Sean Hodkin | 6-0,6-3 |
| ITF M25 Shrewsbury | 2019/09/24 10:25 | Jack Draper v Jhun, Alexander | 6-2,6-4 |
| Challenger - Glasgow | 2019/09/16 17:30 | Jack Draper v Altug Celikbilek | 7-6,4-6,2-6 |
| Sajur, Singles M-ITF-ISR-06A | 2019/09/07 07:00 | Jack Draper v Yshai Oliel | 4-6,6-3,3-6 |
| Challenger Fairfield | 2019/10/09 20:10 | Sarkissian, Alexander v Young, Donald | 6-2,4-6,0-6 |
| Challenger Tiburon | 2019/09/23 23:00 | Young, Donald v Shane, Ryan | 6-1,6-1 |
| Columbus III, USA | 2019/09/19 16:50 | Young, Donald v Quiroz, Roberto | 7-5,4-6,4-6 |
| Columbus III, USA | 2019/09/18 18:10 | Young, Donald v Escobar, Gonzalo | 6-2,6-7,6-1 |
| Challenger Cary | 2019/09/12 16:30 | Young, Donald v Enzo Couacaud | 1-6,6-3,3-6 |
| Challenger Cary | 2019/09/10 16:15 | Young, Donald v Renzo Olivo | 6-4,6-3 |
| New Haven, USA | 2019/09/04 19:20 | Istomin, Denis v Young, Donald | 6-4,6-3 |
| New Haven, USA | 2019/09/02 15:25 | Young, Donald v Filip Peliwo | 6-3,6-4 |