Stadium: Court 8 Round: 26 Ground: Hardcourt outdoor
| Challenger Potchefstroom | 2020/03/11 11:45 | Ortega-Olmedo, Roberto v Jack Draper | 5-7,3-6 |
| ITF - M25 Sunderland | 2020/03/01 12:40 | Jack Draper v Igor Sijsling | 6-2,6-0 |
| ITF - M25 Sunderland | 2020/02/29 10:30 | Valentin Royer v Jack Draper | 2-6,4-6 |
| ITF - M25 Sunderland | 2020/02/28 11:35 | Jack Draper v Dan Added | 6-4,6-2 |
| ITF - M25 Sunderland | 2020/02/27 14:05 | Jack Draper v Evan Furness | 6-4,6-4 |
| ITF M25 Glasgow | 2020/02/23 12:40 | Lucas Poullain v Jack Draper | 0-6,7-5,6-3 |
| ITF M25 Glasgow | 2020/02/22 12:20 | Hoyt, Evan v Jack Draper | 4-6,4-6 |
| ITF M25 Glasgow | 2020/02/21 12:25 | Marek, Wojciech v Jack Draper | 2-6,4-6 |
| Challenger Potchefstroom | 2020/03/11 09:30 | Moundir, Adam v Simon, Tobias | 5-7,3-6 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/08 08:00 | Benjamin Bonzi v Simon, Tobias | 7-6,6-4 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/07 10:00 | Doumbia, Sadio v Simon, Tobias | 6-7,3-6 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/06 08:00 | Corentin Denolly v Simon, Tobias | 1-6,3-6 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/05 11:50 | Simon, Tobias v Daniel Masur | 6-3,3-6,6-3 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/03 09:30 | Carr, Simon v Simon, Tobias | 7-6,6-7,3-6 |
| Challenger Calgary | 2020/02/27 17:00 | Simon, Tobias v Yusuke Takahashi | 4-6,6-7 |
| Challenger Calgary | 2020/02/26 00:10 | Manuel Guinard v Simon, Tobias | 7-6,6-7,6-7 |