Stadium: Stadium 1 Round: 24 Ground: Hardcourt outdoor
| Challenger Binghamton | 2019/07/23 14:00 | Roy Smith v Carlos Gomez-Herrera | 5-7,6-7 |
| Challenger Gatineau | 2019/07/15 19:35 | Kaichi Uchida v Roy Smith | 6-3,6-4 |
| Challenger Winnetka | 2019/07/11 16:00 | Roy Smith v Bjorn Fratangelo | 3-6,3-6 |
| Challenger Winnetka | 2019/07/10 15:00 | Michael Mmoh v Roy Smith | 4-6,4-6 |
| Challenger Winnetka | 2019/07/08 21:15 | Raymond Sarmiento v Roy Smith | 7-6,4-6,0-6 |
| Challenger Columbus | 2019/06/10 20:35 | James Trotter v Roy Smith | 7-6,6-3 |
| Challenger Little Rock | 2019/06/04 15:00 | Tim Smyczek v Roy Smith | 3-6,7-5,6-1 |
| Challenger Little Rock | 2019/06/03 15:00 | Jason Kros v Roy Smith | 1-6,2-6 |
| Challenger Binghamton | 2019/07/25 14:00 | Yuichi Sugita v Edan Leshem | 6-3,7-6 |
| Challenger Binghamton | 2019/07/24 17:50 | Edan Leshem v Marc Polmans | 6-4,6-3 |
| Challenger Binghamton | 2019/07/23 17:50 | Edan Leshem v Diego Hidalgo | 6-4,6-2 |
| Challenger Nur-Sultan | 2019/07/17 05:00 | Yunseong Chung v Edan Leshem | 6-4,4-6,6-4 |
| Challenger Nur-Sultan | 2019/07/16 05:00 | Andrey Golubev v Edan Leshem | 6-7,4-6 |
| ITF M25 Palma del Rio | 2019/06/26 08:30 | Edan Leshem v Jose Fco. Vidal Azorin | 6-3,6-2 |
| Challenger Fergana | 2019/06/20 07:00 | Emil Ruusuvuori v Edan Leshem | 6-3,6-2 |
| Challenger Fergana | 2019/06/19 07:25 | Edan Leshem v Alejandro Tabilo | 6-4,6-4 |