Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF M15 - South Bend | 2023/06/21 20:20 | Aidan Kim v Preston Brown | 6-2,6-2 |
| ITF M15 - Karuizawa | 2023/06/01 03:20 | Preston Brown v Tatsuma Ito | 3-6,0-6 |
| ITF M15 - Karuizawa | 2023/05/31 04:15 | Jesse Delaney v Preston Brown | 2-6,2-6 |
| ITF M15 - Tabasco | 2023/05/24 18:05 | Preston Brown v Ezekiel Clark | 6-3,3-6,0-6 |
| ITF M15 - Tabasco | 2023/05/23 16:00 | Tobias Sonne v Preston Brown | 1-6,1-6 |
| 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 |
| ITF M15 - San Diego | 2023/06/07 15:50 | Ishaan Ravichander v Justin Roberts | 2-6,6-7 |
| ITF M15 - Tabasco | 2023/05/22 23:00 | Joshua Sheehy v Justin Roberts | 6-3,6-3 |
| ITF M25 - Xalapa | 2023/05/16 19:30 | Kousuke Ogura v Justin Roberts | 6-4,6-4 |
| ITF M15 - Tacarigua | 2023/04/25 19:25 | Finn Reynolds v Justin Roberts | 7-6,4-6,6-2 |
| ITF M15 - Tacarigua | 2023/04/20 20:05 | Maxence Broville v Justin Roberts | 5-7,6-2,6-1 |
| ITF M15 - Tacarigua | 2023/04/18 23:20 | Justin Roberts v Joshua Sheehy | 6-2,7-6 |