Stadium: Cancha 1 Round: 24 Ground: Hardcourt outdoor
| Challenger San Luis Potosi | 2019/04/17 20:25 | Pedro Sakamoto v Roberto Ortega-Olmedo | 6-4,6-2 |
| Challenger Murcia | 2019/04/10 09:00 | Roberto Ortega-Olmedo v Enrique Lopez-Perez | 1-6,3-6 |
| Challenger Murcia | 2019/04/08 12:55 | Roberto Ortega-Olmedo v Carlos Lopez Montagud | 6-4,6-1 |
| Challenger Monterrey | 2019/04/02 00:50 | Donald Young v Roberto Ortega-Olmedo | 6-4,6-4 |
| Challenger St Brieuc | 2019/03/26 11:05 | Roberto Ortega-Olmedo v Aslan Karatsev | 4-6,2-6 |
| Challenger Morelos | 2019/02/23 00:00 | Matias Franco Descotte v Roberto Ortega-Olmedo | 7-6,4-6,6-4 |
| Challenger Morelos | 2019/02/21 18:40 | Roberto Ortega-Olmedo v Joao Menezes | 7-6,6-3 |
| Challenger Morelos | 2019/02/19 19:00 | Roberto Ortega-Olmedo v Carlos Boluda-Purkiss | 6-4,6-4 |
| Challenger San Luis Potosi | 2019/04/15 16:00 | Facundo Mena v Yusuke Takahashi | 4-6,6-3,6-0 |
| Challenger Taipei | 2019/04/08 04:00 | Renta Tokuda v Yusuke Takahashi | 6-2,6-1 |
| ITF M15 Kashiwa | 2019/04/06 01:00 | Yuki Mochizuki v Yusuke Takahashi | 7-6,6-4 |
| ITF M15 Kashiwa | 2019/04/05 01:00 | Yusuke Takahashi v Yunosuke Tanaka | 7-5,6-2 |
| ITF M15 Kashiwa | 2019/04/04 01:00 | Yusuke Takahashi v Keisuke Saitoh | 6-2,6-1 |
| ITF M15 Kashiwa | 2019/04/02 02:25 | Yusuke Takahashi v Rio Noguchi | 6-3,3-6,7-5 |
| ITF M15 Kofu | 2019/03/22 03:50 | Yusuke Takahashi v Jumpei Yamasaki | 3-6,1-6 |
| ITF M15 Kofu | 2019/03/21 03:40 | Yusuke Takahashi v Naoki Tajima | 6-3,6-2 |