Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| Challenger New Haven | 2019/09/04 17:00 | Andreas Seppi v Roy Smith | 7-6,6-3 |
| Challenger New Haven | 2019/09/03 17:30 | Felix Corwin v Roy Smith | 3-6,6-1,4-6 |
| 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 Columbus 3 | 2019/09/17 14:00 | Jacob Dunbar v Ryan Shane | 5-7,4-6 |
| Challenger New Haven | 2019/09/04 14:00 | Mitchell Krueger v Ryan Shane | 3-6,4-6 |
| Challenger New Haven | 2019/09/02 14:00 | Aleksandar Kovacevic v Ryan Shane | 4-6,4-6 |
| ITF M25 Edwardsville | 2019/08/07 16:10 | Ryan Shane v Jacob Dunbar | 2-6,2-6 |
| Challenger Lexington | 2019/07/30 14:30 | Ryan Shane v Vasil Kirkov | 3-6,6-1,3-6 |
| Challenger Binghamton | 2019/07/23 16:30 | Ryan Shane v Alejandro Tabilo | 3-6,4-6 |
| Challenger Winnetka | 2019/07/09 01:50 | Sekou Bangoura v Ryan Shane | 7-5,6-3 |
| Challenger Columbus | 2019/06/11 20:45 | Ryan Shane v Matias Franco Descotte | 6-7,6-7 |