Stadium: Estadio Sid Round: 14 Ground: Clay
| ITF M25 Laval | 2023/07/11 14:15 | Preston Brown v Justin Roberts | 6-3,7-6 |
| ITF M15 Pittsburgh | 2023/07/26 14:00 | A.J Catanzariti v Preston Brown | 6-3,6-4 |
| ITF M15 Rochester | 2023/07/20 17:00 | Preston Brown v A.J Catanzariti | 1-6,6-3,3-6 |
| ITF M15 Rochester | 2023/07/18 22:30 | Herbert Jody Maginley v Preston Brown | 0-6,2-6 |
| ITF M25 Laval | 2023/07/13 16:00 | Preston Brown v Alexander Cozbinov | 2-6,1-6 |
| ITF M25 Laval | 2023/07/11 14:15 | Preston Brown v Justin Roberts | 6-3,7-6 |
| Challenger Santa Fe | 2023/07/03 16:25 | Pedro Boscardin Dias v Preston Brown | 7-6,6-3 |
| Challenger Medellin | 2023/06/26 21:30 | Aidan Mayo v Preston Brown | 7-5,6-3 |
| Challenger Medellin | 2023/06/26 18:25 | Preston Brown v Alejandro H Franco | 6-1,6-4 |
| Challenger Lexington | 2023/07/31 14:00 | Philip Sekulic v Justin Roberts | 6-1,6-4 |
| Challenger Lexington | 2023/07/30 15:05 | Justin Roberts v Ramkumar Ramanathan | 7-6,7-6 |
| ITF M15 Rochester | 2023/07/21 18:50 | Ignacio Monzon v Justin Roberts | 6-4,6-2 |
| ITF M15 Rochester | 2023/07/20 15:25 | Yannik Rahman v Justin Roberts | 1-6,2-6 |
| ITF M15 Rochester | 2023/07/19 14:30 | Maksim Tikhomirov v Justin Roberts | 1-6,4-6 |
| ITF M25 Laval | 2023/07/11 14:15 | Preston Brown v Justin Roberts | 6-3,7-6 |
| ITF M15 South Bend | 2023/06/21 15:00 | Justin Roberts v Axel Nefve | 1-6,1-6 |
| ITF M15 San Diego | 2023/06/08 18:35 | Justin Roberts v Jack Anthrop | 3-6,4-6 |