Stadium: Cancha 1 Round: 24 Ground: Hardcourt outdoor
| ATP - Indian Wells | 2019/03/08 19:00 | Young, Donald v Hubert Hurkacz | 3-6,3-6 |
| Challenger - Indian Wells | 2019/02/28 18:00 | Young, Donald v Lloyd Harris | 4-6,2-6 |
| Challenger - Indian Wells | 2019/02/26 21:45 | Laaksonen, Henri v Young, Donald | 5-7,6-3,4-6 |
| Challenger - Indian Wells | 2019/02/25 19:30 | Thai-Son Kwiatkowski v Young, Donald | 6-4,1-6,6-7 |
| ATP - Delray Beach | 2019/02/17 17:45 | Young, Donald v Daniel Evans | 2-6,6-7 |
| ATP - Delray Beach | 2019/02/16 18:35 | Fratangelo, Bjorn v Young, Donald | 2-6,6-7 |
| Challenger - Cleveland | 2019/01/30 02:55 | Smith, Roy v Young, Donald | 6-4,0-6,7-6 |
| Newport Beach, USA | 2019/01/26 18:00 | Schnur, Brayden v Young, Donald | 6-2,3-6,7-6 |
| Challenger St Brieuc | 2019/03/26 11:05 | Ortega-Olmedo, Roberto v Karatsev, Aslan | 4-6,2-6 |
| Challenger - Morelos | 2019/02/23 00:00 | Matias Franco Descotte v Ortega-Olmedo, Roberto | 7-6,4-6,6-4 |
| Challenger - Morelos | 2019/02/21 18:40 | Ortega-Olmedo, Roberto v Joao Menezes | 7-6,6-3 |
| Challenger - Morelos | 2019/02/19 19:00 | Ortega-Olmedo, Roberto v Boluda-Purkiss, Carlos | 6-4,6-4 |
| Challenger - Cherbourg | 2019/02/11 10:00 | Ortega-Olmedo, Roberto v Zdenek Kolar | 1-6,2-6 |
| Challenger - Quimper | 2019/01/28 10:50 | Mathias Bourgue v Ortega-Olmedo, Roberto | 4-6,7-6,6-4 |
| Challenger - Koblenz | 2019/01/20 13:00 | Gianluca Mager v Ortega-Olmedo, Roberto | 2-6,7-6,6-2 |
| Challenger - Koblenz | 2019/01/19 16:00 | Pavel Kotov v Ortega-Olmedo, Roberto | 5-7,6-3,3-6 |