Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger - Bangkok | 2020/01/14 04:45 | Jack Draper v Denis Istomin | 4-6,2-6 |
| Challenger - Bangkok | 2020/01/12 06:40 | Jack Draper v Yunseong Chung | 7-6,6-3 |
| 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 |
| ITF M15 - Monastir | 2019/12/17 16:20 | Kristjan Tamm v Thomas Laurent | 3-6,1-6 |
| ITF M15 - Monastir | 2019/12/13 09:00 | Thomas Laurent v Kristjan Tamm | 6-2,6-3 |
| ITF M15 - Monastir | 2019/12/12 12:00 | Fabien Reboul v Kristjan Tamm | 6-4,3-6,6-7 |
| ITF M15 - Monastir | 2019/12/11 08:30 | Kristjan Tamm v Giorgio Ricca | 3-6,7-6,6-4 |
| ITF M15 - Monastir | 2019/11/17 09:00 | Andrea Guerrieri v Kristjan Tamm | 3-6,1-6 |
| ITF M15 - Monastir | 2019/11/16 09:00 | Kristjan Tamm v Daniele Capecchi | 0-6,6-3,6-2 |
| ITF M15 - Monastir | 2019/11/15 08:30 | Benjamin Winter Lopez v Kristjan Tamm | 3-6,6-3,1-6 |
| ITF M15 - Monastir | 2019/11/14 11:15 | Kristjan Tamm v Ivan Davydov | 6-1,6-4 |