Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Aptos | 2019/08/07 18:55 | Damir Dzumhur v Keegan Smith | 6-4,6-4 |
| Challenger Aptos | 2019/08/06 17:00 | Keegan Smith v Brandon Holt | 6-4,6-3 |
| Challenger Aptos | 2019/08/05 17:00 | Sem Verbeek v Keegan Smith | 5-7,1-6 |
| Challenger Lexington | 2019/07/30 23:00 | Keegan Smith v Liam Draxl | 4-6,6-7 |
| Challenger Lexington | 2019/07/29 14:00 | Bernardo Saraiva v Keegan Smith | 5-7,3-6 |
| ITF M15 Rochester | 2019/06/26 20:25 | Zachary Svajda v Keegan Smith | 6-2,7-6 |
| ITF M25 Calabasas | 2019/03/22 02:25 | Keegan Smith v Jonathan Gray | 3-6,7-6,1-6 |
| ITF M25 Calabasas | 2019/03/20 20:40 | Sekou Bangoura v Keegan Smith | 6-7,6-4,5-7 |
| ITF M15 Ystad | 2019/08/07 08:15 | Simon Freund v Juan Manuel Cerundolo | 2-6,6-7 |
| ITF M15 Pittsburgh | 2019/07/07 15:00 | Alexander Cozbinov v Simon Freund | 2-6,6-2,6-1 |
| ITF M15 Pittsburgh | 2019/07/06 17:00 | Paul Oosterbaan v Simon Freund | 1-6,1-6 |
| ITF M15 Pittsburgh | 2019/07/04 15:25 | Simon Freund v Ricardo Rodriguez-Pace | 3-6,6-1,7-5 |
| ITF M15 Pittsburgh | 2019/07/02 14:00 | John Harrison Richmond v Simon Freund | 4-6,3-6 |
| ITF M15 Rochester | 2019/06/29 19:00 | Simon Freund v Strong Kirchheimer | 1-6,5-7 |
| ITF M15 Rochester | 2019/06/28 18:15 | Simon Freund v Ronan Jachuck | 6-2,6-4 |
| ITF M15 Rochester | 2019/06/27 18:40 | Simon Freund v Zachary Svajda | 6-4,0-6,6-3 |