Stadium: Court 1 Round: 14 Ground: Hardcourt outdoor
| Challenger Cary | 2023/08/06 14:00 | Strong Kirchheimer v Quinn Vandecasteele | 7-5,3-6,2-6 |
| Challenger Lexington | 2023/08/03 01:00 | Tennys Sandgren v Strong Kirchheimer | 6-2,6-4 |
| Challenger Lexington | 2023/07/31 20:00 | Strong Kirchheimer v Martin Damm | 6-7,7-6,7-6 |
| Challenger Granby | 2023/07/16 15:00 | Strong Kirchheimer v James Trotter | 6-7,4-6 |
| Challenger Chicago | 2023/07/09 19:05 | Strong Kirchheimer v Colin Sinclair | 6-7,4-6 |
| Challenger Bloomfield Hills | 2023/07/03 16:25 | Yunseong Chung v Strong Kirchheimer | 6-4,7-6 |
| ITF M15 South Bend | 2023/06/25 15:00 | Strong Kirchheimer v James Tracy | 1-6,2-6 |
| ITF M15 South Bend | 2023/06/24 14:55 | Strong Kirchheimer v Blaise Bicknell | 7-5,7-6 |
| ITF M15 Pittsburgh | 2023/07/30 18:45 | Darian King v Juan Carlos Aguilar | 4-6,6-3,6-3 |
| ITF M15 Pittsburgh | 2023/07/30 14:00 | Felix Corwin v Juan Carlos Aguilar | 3-6,4-6 |
| ITF M15 Pittsburgh | 2023/07/28 14:50 | Jesse Flores v Juan Carlos Aguilar | 6-4,1-6,3-6 |
| ITF M15 Pittsburgh | 2023/07/27 15:00 | Juan Carlos Aguilar v Nick Lagaev | 6-4,6-4 |
| ITF M15 Pittsburgh | 2023/07/25 16:00 | Juan Carlos Aguilar v Henrik Wiersholm | 6-4,7-6 |
| ITF M15 Rochester | 2023/07/20 19:20 | Juan Carlos Aguilar v Nicholas Heng | 3-6,4-6 |
| ITF M15 Rochester | 2023/07/19 16:25 | Juan Carlos Aguilar v Jonathan Sorbo | 6-4,6-2 |
| ITF M25 Bakio | 2023/06/27 13:20 | Juan Carlos Aguilar v Pedro Vives Marcos | 6-7,1-6 |