Stadium: Court 1 Round: 24 Ground: Hardcourt outdoor
| Challenger New Haven | 2019/09/02 14:00 | Felix Corwin v Michael Sun | 6-4,6-3 |
| ITF M25 - Edwardsville | 2019/08/09 16:55 | Petros Chrysochos v Felix Corwin | 1-6,6-4,6-3 |
| ITF M25 - Edwardsville | 2019/08/08 16:15 | Felix Corwin v Austin Rapp | 6-4,6-4 |
| ITF M25 - Edwardsville | 2019/08/07 19:25 | Joshua Howard-Tripp v Felix Corwin | 0-6,4-6 |
| ITF M25 - Decatur | 2019/08/01 22:00 | Hady Habib v Felix Corwin | 6-3,6-4 |
| ITF M25 - Decatur | 2019/07/31 18:40 | Gui Gomes v Felix Corwin | 1-6,3-6 |
| ITF M15 - Cancun | 2019/07/26 13:30 | Felix Corwin v Jean Thirouin | 5-7,0-6 |
| ITF M15 - Cancun | 2019/07/25 13:30 | Felix Corwin v Peter Bertran | 6-4,6-3 |
| ATP Winston-Salem | 2019/08/17 18:00 | Marcos Giron v Roy Smith | 6-2,6-0 |
| Challenger Lexington | 2019/08/01 23:50 | Roy Smith v Alex Bolt | 6-3,3-6,4-6 |
| Challenger Lexington | 2019/07/31 19:20 | Collin Altamirano v Roy Smith | 4-6,7-6,2-6 |
| Challenger Lexington | 2019/07/30 01:10 | Roy Smith v Edan Leshem | 7-6,7-6 |
| 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 |