Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| Challenger Ann Arbor | 2020/01/09 16:00 | Pedro Sakamoto v Edan Leshem | 6-4,3-6,5-7 |
| Challenger Ann Arbor | 2020/01/10 21:35 | Daniel Altmaier v Edan Leshem | 7-6,7-5 |
| Challenger Ann Arbor | 2020/01/09 16:00 | Pedro Sakamoto v Edan Leshem | 6-4,3-6,5-7 |
| Challenger Ann Arbor | 2020/01/07 20:35 | Edan Leshem v Sebastian Korda | 7-5,6-3 |
| Challenger Ann Arbor | 2020/01/06 21:25 | Edan Leshem v Julian Ocleppo | 6-4,6-3 |
| Challenger Houston | 2019/11/13 18:30 | Tennys Sandgren v Edan Leshem | 6-3,7-5 |
| Challenger Houston | 2019/11/11 17:20 | Edan Leshem v Christopher Heyman | 6-4,6-4 |
| Challenger Knoxville | 2019/11/06 18:40 | Peter Polansky v Edan Leshem | 6-2,7-5 |
| Challenger Knoxville | 2019/11/05 19:45 | Blaz Kavcic v Edan Leshem | 2-6,6-7 |
| Challenger Ann Arbor | 2020/01/09 16:00 | Pedro Sakamoto v Edan Leshem | 6-4,3-6,5-7 |
| Challenger Ann Arbor | 2020/01/07 21:50 | Pedro Sakamoto v Alexey Zakharov | 6-2,7-6 |
| ITF M25 Naples | 2019/11/20 19:55 | Pedro Sakamoto v Martin Damm | 4-6,4-6 |
| ITF M25 Orlando | 2019/11/17 17:45 | Nicolas Alvarez v Pedro Sakamoto | 3-6,6-2,6-1 |
| ITF M25 Orlando | 2019/11/16 16:00 | Tomas Martin Etcheverry v Pedro Sakamoto | 6-4,1-6,2-6 |
| ITF M25 Orlando | 2019/11/15 19:00 | Adam Moundir v Pedro Sakamoto | 6-3,3-6,4-6 |
| ITF M25 Orlando | 2019/11/14 15:00 | Adrian Andreev v Pedro Sakamoto | 4-6,2-6 |
| ITF M25 Orlando | 2019/11/12 19:25 | Jose Olivares v Pedro Sakamoto | 2-6,3-6 |