Stadium: Center Court Round: 24 Ground: Hardcourt indoor
| Challenger Monterrey | 2019/04/02 00:50 | Donald Young v Roberto Ortega-Olmedo | 6-4,6-4 |
| Challenger Dallas | 2020/02/06 03:30 | Mackenzie McDonald v Donald Young | 6-4,1-6,6-4 |
| Challenger Dallas | 2020/02/04 19:15 | Stefan Kozlov v Donald Young | 2-6,2-6 |
| Challenger Newport Beach | 2020/01/29 23:25 | Donald Young v Mitchell Krueger | 6-3,1-6,4-6 |
| Challenger Newport Beach | 2020/01/27 22:55 | Donald Young v Brandon Nakashima | 1-6,7-6,6-4 |
| Australian Open | 2020/01/14 03:45 | Donald Young v Jason Jung | 4-6,7-6,1-6 |
| Challenger Houston | 2019/11/13 16:00 | Alexis Galarneau v Donald Young | 3-6,6-3,6-0 |
| Challenger Knoxville | 2019/11/05 01:00 | Liam Broady v Donald Young | 7-6,6-3 |
| Challenger Charlottesville | 2019/10/28 20:45 | Donald Young v Blaz Kavcic | 3-6,6-7 |
| Challenger Quimper | 2020/01/30 13:40 | Roberto Ortega-Olmedo v Lukas Lacko | 2-6,2-6 |
| Challenger Quimper | 2020/01/28 10:35 | Roberto Ortega-Olmedo v Luca Vanni | 7-6,6-1 |
| Challenger Rennes | 2020/01/24 18:40 | Tobias Kamke v Roberto Ortega-Olmedo | 6-3,6-3 |
| Challenger Rennes | 2020/01/23 18:35 | Roberto Ortega-Olmedo v Evan Furness | 4-6,6-2,7-5 |
| Challenger Rennes | 2020/01/21 10:30 | Roberto Ortega-Olmedo v Dan Added | 7-6,6-3 |
| Australian Open | 2020/01/16 03:40 | Roberto Ortega-Olmedo v Filip Horansky | 6-4,5-7,4-6 |
| ITF M15 Cairo | 2019/11/30 08:00 | Roberto Ortega-Olmedo v Daniel Michalski | 4-6,4-6 |
| ITF M15 Cairo | 2019/11/29 10:55 | Roberto Ortega-Olmedo v Peter Nagy | 6-1,6-3 |