Stadium: Court 5 Round: 14 Ground: Hardcourt outdoor
| Challenger Tyler | 2023/06/08 19:20 | Tennys Sandgren v Nick Chappell | 6-3,6-4 |
| Challenger Tyler | 2023/06/06 18:05 | Omni Kumar v Nick Chappell | 4-6,2-6 |
| Challenger Tyler | 2023/06/05 16:30 | Rubin Statham v Nick Chappell | 5-7,5-7 |
| Challenger Tyler | 2023/06/04 17:05 | Bernard Tomic v Nick Chappell | 5-7,3-6 |
| Challenger Little Rock | 2023/05/28 17:55 | Giles Hussey v Nick Chappell | 6-4,7-6 |
| Challenger Savannah | 2023/04/25 14:00 | Nick Chappell v Alex Rybakov | 2-6,3-6 |
| Challenger Tallahassee | 2023/04/18 16:40 | Nick Chappell v Dmitry Popko | 3-6,4-6 |
| Challenger Leon | 2023/04/11 23:50 | Nick Chappell v Giovanni Mpetshi Perricard | 1-6,6-4,2-6 |
| Challenger Tyler | 2023/06/05 16:30 | Tristan Boyer v Marius Copil | 4-6,6-3,5-7 |
| Challenger Tyler | 2023/06/04 15:00 | Tristan Schoolkate v Tristan Boyer | 4-6,1-6 |
| Challenger Little Rock | 2023/05/29 20:00 | Evan Zhu v Tristan Boyer | 6-4,6-7,7-6 |
| Challenger Savannah | 2023/04/30 20:00 | Tristan Boyer v Facundo Diaz Acosta | 3-6,1-6 |
| Challenger Savannah | 2023/04/29 20:35 | Calvin Hemery v Tristan Boyer | 6-2,4-6,3-6 |
| Challenger Savannah | 2023/04/28 19:40 | Tristan Boyer v Mitchell Krueger | 6-4,6-1 |
| Challenger Savannah | 2023/04/27 15:00 | Tristan Boyer v Mateus Alves | 6-1,6-4 |
| Challenger Savannah | 2023/04/25 17:25 | Enzo Couacaud v Tristan Boyer | 2-6,3-6 |