Stadium: Stadium Court Round: 25 Ground: Clay
| ATP Houston | 2019/04/07 15:00 | Christopher Eubanks v Santiago Giraldo | 4-6,4-6 |
| ATP Houston | 2019/04/06 19:00 | Santiago Giraldo v James Ward | 6-4,6-4 |
| Challenger Monterrey | 2019/04/04 23:05 | Donald Young v Santiago Giraldo | 6-3,6-4 |
| Challenger Monterrey | 2019/04/03 19:20 | Santiago Giraldo v Roberto Quiroz | 3-6,7-5,7-6 |
| Challenger Monterrey | 2019/04/01 22:50 | Roberto Cid Subervi v Santiago Giraldo | 6-7,3-6 |
| Challenger Indian Wells | 2019/02/28 19:50 | Daniel Evans v Santiago Giraldo | 6-1,6-2 |
| Challenger Indian Wells | 2019/02/27 20:20 | Santiago Giraldo v Jared Donaldson | 6-2,2-6,6-4 |
| Challenger Indian Wells | 2019/02/25 23:30 | Santiago Giraldo v Dennis Novikov | 7-5,5-7,6-2 |
| Challenger Monterrey | 2019/04/05 21:55 | Donald Young v Bradley Klahn | 7-5,6-4 |
| 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 |