Stadium: Cancha 1 Round: 25 Ground: Hardcourt outdoor
| ATP Miami | 2019/03/20 14:00 | Felix Auger Aliassime v Paolo Lorenzi | 7-6,6-2 |
| ATP Miami | 2019/03/18 16:40 | Ruben Bemelmans v Paolo Lorenzi | 5-7,6-3,6-7 |
| ATP Sao Paulo | 2019/02/26 16:00 | Paolo Lorenzi v Juan Ignacio Londero | 6-7,1-6 |
| ATP Delray Beach | 2019/02/21 18:00 | Steve Johnson v Paolo Lorenzi | 7-5,7-5 |
| ATP Delray Beach | 2019/02/19 18:35 | Tim Smyczek v Paolo Lorenzi | 5-7,3-6 |
| ATP Nowy Jork | 2019/02/15 17:00 | Paolo Lorenzi v Brayden Schnur | 7-6,6-7,5-7 |
| ATP Nowy Jork | 2019/02/13 17:55 | Paolo Lorenzi v Ryan Harrison | 4-6,6-4,6-4 |
| ATP Nowy Jork | 2019/02/11 19:55 | Tennys Sandgren v Paolo Lorenzi | 6-7,7-6,4-6 |
| 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 |
| ATP Delray Beach | 2019/02/16 18:35 | Bjorn Fratangelo v Donald Young | 2-6,6-7 |
| Challenger Cleveland | 2019/01/30 02:55 | Roy Smith v Donald Young | 6-4,0-6,7-6 |