Stadium: Court 1 Round: 24 Ground: Hardcourt indoor
| Challenger Indian Wells | 2019/02/26 18:00 | Michael Redlicki v Ernesto Escobedo | 3-6,6-7 |
| Challenger Indian Wells | 2019/02/25 18:00 | Alexander Sarkissian v Michael Redlicki | 3-6,3-6 |
| Challenger Morelos | 2019/02/20 02:00 | Santiago Giraldo v Michael Redlicki | 6-4,7-5 |
| Challenger Morelos | 2019/02/18 18:55 | Michael Redlicki v Tak Khunn Wang | 4-6,6-2,7-5 |
| Challenger Dallas | 2019/02/05 22:55 | Brayden Schnur v Michael Redlicki | 7-6,6-4 |
| Challenger Dallas | 2019/02/05 00:35 | Goncalo Oliveira v Michael Redlicki | 2-6,6-4,1-6 |
| Challenger Cleveland | 2019/01/29 00:25 | Michael Redlicki v Borna Gojo | 3-6,7-6,4-6 |
| Challenger Orlando | 2019/01/05 19:50 | Darian King v Michael Redlicki | 6-4,6-2 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Roy Smith | 6-3,6-3 |
| ATP New York | 2019/02/10 21:20 | Ramkumar Ramanathan v Roy Smith | 4-6,6-2,6-4 |
| Challenger Cleveland | 2019/01/30 02:55 | Roy Smith v Donald Young | 6-4,0-6,7-6 |
| 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 |