Stadium: Stadium Court Round: 25 Ground: Clay
| ATP - Houston | 2019/04/07 15:00 | Christopher Eubanks v Giraldo, Santiago | 4-6,4-6 |
| ATP - Houston | 2019/04/06 19:00 | Giraldo, Santiago v Ward, James | 6-4,6-4 |
| Monterrey, Mexico | 2019/04/04 23:05 | Young, Donald v Giraldo, Santiago | 6-3,6-4 |
| Monterrey, Mexico | 2019/04/03 19:20 | Giraldo, Santiago v Quiroz, Roberto | 3-6,7-5,7-6 |
| Monterrey, Mexico | 2019/04/01 22:50 | Roberto Cid Subervi v Giraldo, Santiago | 6-7,3-6 |
| Challenger - Indian Wells | 2019/02/28 19:50 | Daniel Evans v Giraldo, Santiago | 6-1,6-2 |
| Challenger - Indian Wells | 2019/02/27 20:20 | Giraldo, Santiago v Donaldson, Jared | 6-2,2-6,6-4 |
| Challenger - Indian Wells | 2019/02/25 23:30 | Giraldo, Santiago v Novikov, Dennis | 7-5,5-7,6-2 |
| Monterrey, Mexico | 2019/04/05 21:55 | Young, Donald v Klahn, Bradley | 7-5,6-4 |
| Monterrey, Mexico | 2019/04/04 17:00 | Sebastian Ofner v Klahn, Bradley | 3-6,3-6 |
| Monterrey, Mexico | 2019/04/03 18:50 | Song, Evan v Klahn, Bradley | 4-6,3-6 |
| ATP - Miami | 2019/03/20 18:50 | Tipsarevic, Janko v Klahn, Bradley | 6-3,6-3 |
| ATP - Indian Wells | 2019/03/08 02:00 | Klahn, Bradley v Jaziri, Malek | 4-6,2-6 |
| Open d'Australie | 2019/01/15 01:40 | Chung, Hyeon v Klahn, Bradley | 6-7,6-7,6-3,6-2,6-4 |
| ATP - Auckland | 2019/01/07 00:15 | Kohlschreiber, Philipp v Klahn, Bradley | 6-4,7-6 |
| ATP - Auckland | 2019/01/05 22:00 | Klahn, Bradley v Cuevas, Pablo | 6-7,7-6,7-6 |