Stadium: Court 2 Round: 25 Ground: Hardcourt indoor
| Challenger Cleveland | 2019/01/28 18:25 | Roy Smith v Gijs Brouwer | 7-6,6-3 |
| Challenger Newport Beach | 2019/01/21 19:30 | Roy Smith v Benjamin Bonzi | 2-6,5-7 |
| Challenger Canberra | 2019/01/07 04:15 | Tomas Barrios Vera v Roy Smith | 7-6,6-3 |
| Challenger Noumea | 2018/12/31 06:15 | Marc-Andrea Huesler v Roy Smith | 6-4,7-6 |
| Challenger Houston | 2018/11/19 01:00 | Roy Smith v Bradley Klahn | 6-7,6-7 |
| Challenger Houston | 2018/11/16 17:50 | Thai-Son Kwiatkowski v Roy Smith | 6-4,6-7,6-7 |
| Challenger Houston | 2018/11/14 16:00 | Roy Smith v Harrison Adams | 6-3,6-4 |
| Challenger Houston | 2018/11/13 19:45 | Darian King v Roy Smith | 3-6,6-3,6-7 |
| Challenger Newport Beach | 2019/01/26 18:00 | Brayden Schnur v Donald Young | 6-2,3-6,7-6 |
| Challenger Newport Beach | 2019/01/25 22:55 | Donald Young v Collin Altamirano | 6-2,6-1 |
| Challenger Newport Beach | 2019/01/24 20:40 | JC Aragone v Donald Young | 3-6,4-6 |
| Challenger Newport Beach | 2019/01/22 19:45 | Donald Young v Noah Rubin | 6-4,6-3 |
| Challenger Newport Beach | 2019/01/21 18:00 | Patrick Kypson v Donald Young | 3-6,2-6 |
| Australian Open | 2019/01/09 00:50 | Donald Young v Enrique Lopez-Perez | 7-5,1-6,2-6 |
| Challenger Noumea | 2019/01/05 02:00 | Noah Rubin v Donald Young | 6-2,6-3 |
| Challenger Noumea | 2019/01/04 02:35 | Gleb Sakharov v Donald Young | 7-5,3-6,1-6 |