Stadium: Court 2 Round: 26 Ground: Hardcourt indoor
| Challenger Helsinki | 2019/11/12 13:25 | Elias Ymer v Jack Draper | 6-3,3-6,6-4 |
| Challenger Helsinki | 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 |
| ITF M15 Heraklion | 2019/12/01 09:00 | Mason Recci v Leopold Zima | 6-1,7-5 |
| ITF M15 Heraklion | 2019/11/27 09:30 | Leopold Zima v Guy Den Heijer | 3-6,0-6 |
| ITF M15 Heraklion | 2019/11/26 08:00 | Athanassios Manekas v Leopold Zima | 7-5,4-6,7-10 |
| ITF M15 Heraklion | 2019/11/25 09:00 | Leopold Zima v Pavel Shumeiko | 6-1,7-5 |
| ITF M15 Heraklion | 2019/11/24 10:30 | Ido Zonder v Leopold Zima | 3-6,2-6 |
| Challenger Eckental | 2019/10/28 12:50 | Leopold Zima v Jurij Rodionov | 4-6,6-7 |
| ITF M15 Doha | 2019/10/22 14:05 | Marek Semjan v Leopold Zima | 6-2,2-6,10-7 |
| ITF M15 Doha | 2019/10/21 15:25 | Erik Helin v Leopold Zima | 3-6,1-6 |