Stadium: Brenda Meyers Court Round: 24 Ground: Hardcourt indoor
| Challenger Las Vegas | 2019/10/16 17:30 | Roy Smith v James Duckworth | 4-6,4-6 |
| Challenger Las Vegas | 2019/10/15 17:30 | Roy Smith v Marcelo Arevalo | 6-2,4-6,6-3 |
| Challenger Fairfield | 2019/10/07 19:15 | Roy Smith v JC Aragone | 6-7,4-6 |
| ITF M25 Norman | 2019/10/01 18:20 | Roy Smith v Lucas Gerch | 5-7,4-6 |
| Challenger Tiburon | 2019/09/23 18:25 | Roy Smith v Gonzalo Escobar | 2-6,6-3,2-6 |
| Challenger Columbus 3 | 2019/09/19 16:45 | Roy Smith v Peter Polansky | 4-6,4-6 |
| Challenger Columbus 3 | 2019/09/18 15:40 | Roy Smith v Ryan Shane | 4-6,6-4,6-4 |
| Challenger New Haven | 2019/09/04 17:00 | Andreas Seppi v Roy Smith | 7-6,6-3 |
| Challenger Charlottesville | 2019/10/28 14:00 | Liam Caruana v Cannon Kingsley | 6-3,7-6 |
| ITF M25 Fayetteville | 2019/10/23 18:00 | Nick Chappell v Liam Caruana | 7-5,6-4 |
| ITF M25 Waco | 2019/10/17 16:00 | Nick Chappell v Liam Caruana | 6-4,6-4 |
| ITF M25 Waco | 2019/10/16 14:45 | Liam Caruana v Zachary Svajda | 6-3,6-3 |
| ITF M25 Harlingen | 2019/09/28 01:00 | Alex Rybakov v Liam Caruana | 7-5,6-4 |
| ITF M25 Harlingen | 2019/09/27 00:35 | Nathan Ponwith v Liam Caruana | 4-6,6-4,4-10 |
| ITF M25 Harlingen | 2019/09/25 14:55 | Liam Caruana v Mark Whitehouse | 6-3,6-7,6-3 |
| ITF M25 Houston | 2019/09/22 16:15 | Liam Caruana v Hugo Gaston | 1-6,3-6 |