Stadium: Stadium Round: 14 Ground: Hardcourt outdoor
| Challenger Stanford | 2023/08/16 18:25 | James Duckworth v Adam Walton | 6-3,6-4 |
| Challenger Stanford | 2023/08/15 17:00 | Zachary Svajda v Adam Walton | 2-6,2-6 |
| Challenger Cary | 2023/08/13 18:00 | Nicolas Moreno De Alboran v Adam Walton | 4-6,6-3,5-7 |
| Challenger Cary | 2023/08/12 19:00 | Liam Broady v Adam Walton | 4-6,5-7 |
| Challenger Cary | 2023/08/11 19:30 | Adam Walton v Rinky Hijikata | 6-2,6-4 |
| Challenger Cary | 2023/08/09 18:00 | Billy Harris v Adam Walton | 6-3,6-7,6-7 |
| Challenger Cary | 2023/08/07 20:25 | Beibit Zhukayev v Adam Walton | 4-6,3-6 |
| Challenger Lexington | 2023/08/02 14:00 | Adam Walton v Ulises Blanch | 3-6,3-6 |
| Challenger Winnipeg | 2023/08/15 20:50 | Strong Kirchheimer v Liam Broady | 3-6,3-6 |
| Challenger Winnipeg | 2023/08/14 18:20 | Strong Kirchheimer v Alafia Ayeni | 7-5,6-2 |
| Challenger Winnipeg | 2023/08/13 18:45 | Strong Kirchheimer v Juan Carlos Aguilar | 1-6,6-4,6-4 |
| 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 |