Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| New Haven, USA | 2019/09/04 17:00 | Seppi, Andreas v Smith, Roy | 7-6,6-3 |
| New Haven, USA | 2019/09/03 17:30 | Felix Corwin v Smith, Roy | 3-6,6-1,4-6 |
| Winston-Salem, USA | 2019/08/17 18:00 | Marcos Giron v Smith, Roy | 6-2,6-0 |
| Challenger Lexington | 2019/08/01 23:50 | Smith, Roy v Alex Bolt | 6-3,3-6,4-6 |
| Challenger Lexington | 2019/07/31 19:20 | Collin Altamirano v Smith, Roy | 4-6,7-6,2-6 |
| Challenger Lexington | 2019/07/30 01:10 | Smith, Roy v Edan Leshem | 7-6,7-6 |
| Binghamton, USA | 2019/07/23 14:00 | Smith, Roy v Gomez-Herrera, Carlos | 5-7,6-7 |
| Gatineau, Canada | 2019/07/15 19:35 | Kaichi Uchida v Smith, Roy | 6-3,6-4 |
| Columbus III, USA | 2019/09/17 14:00 | Dunbar, Jacob v Shane, Ryan | 5-7,4-6 |
| New Haven, USA | 2019/09/04 14:00 | Mitchell Krueger v Shane, Ryan | 3-6,4-6 |
| New Haven, USA | 2019/09/02 14:00 | Aleksandar Kovacevic v Shane, Ryan | 4-6,4-6 |
| ITF M25 Edwardsville | 2019/08/07 16:10 | Shane, Ryan v Dunbar, Jacob | 2-6,2-6 |
| Challenger Lexington | 2019/07/30 14:30 | Shane, Ryan v Kirkov, Vasil | 3-6,6-1,3-6 |
| Binghamton, USA | 2019/07/23 16:30 | Shane, Ryan v Alejandro Tabilo | 3-6,4-6 |
| Winnetka, USA | 2019/07/09 01:50 | Bangoura, Sekou v Shane, Ryan | 7-5,6-3 |
| Challenger Columbus | 2019/06/11 20:45 | Shane, Ryan v Matias Franco Descotte | 6-7,6-7 |