Stadium: Cancha 1 Round: 27 Ground: Hardcourt outdoor
| Challenger Monterrey | 2019/04/04 23:05 | Donald Young v Santiago Giraldo | 6-3,6-4 |
| Challenger Monterrey | 2019/04/04 00:45 | Paolo Lorenzi v Donald Young | 4-6,3-6 |
| Challenger Monterrey | 2019/04/02 00:50 | Donald Young v Roberto Ortega-Olmedo | 6-4,6-4 |
| ATP Indian Wells | 2019/03/08 19:00 | Donald Young v Hubert Hurkacz | 3-6,3-6 |
| Challenger Indian Wells | 2019/02/28 18:00 | Donald Young v Lloyd Harris | 4-6,2-6 |
| Challenger Indian Wells | 2019/02/26 21:45 | Henri Laaksonen v Donald Young | 5-7,6-3,4-6 |
| Challenger Indian Wells | 2019/02/25 19:30 | Thai-Son Kwiatkowski v Donald Young | 6-4,1-6,6-7 |
| ATP Delray Beach | 2019/02/17 17:45 | Donald Young v Daniel Evans | 2-6,6-7 |
| Challenger Monterrey | 2019/04/04 17:00 | Sebastian Ofner v Bradley Klahn | 3-6,3-6 |
| Challenger Monterrey | 2019/04/03 18:50 | Evan Song v Bradley Klahn | 4-6,3-6 |
| ATP Miami | 2019/03/20 18:50 | Janko Tipsarevic v Bradley Klahn | 6-3,6-3 |
| ATP Indian Wells | 2019/03/08 02:00 | Bradley Klahn v Malek Jaziri | 4-6,2-6 |
| Australian Open | 2019/01/15 01:40 | Hyeon Chung v Bradley Klahn | 6-7,6-7,6-3,6-2,6-4 |
| ATP Auckland | 2019/01/07 00:15 | Philipp Kohlschreiber v Bradley Klahn | 6-4,7-6 |
| ATP Auckland | 2019/01/05 22:00 | Bradley Klahn v Pablo Cuevas | 6-7,7-6,7-6 |
| ATP Auckland | 2019/01/04 22:00 | Bradley Klahn v Philipp Oswald | 7-6,6-4 |