Stadium: Brenda Meyers Court Round: 14 Ground: Hardcourt indoor
| Challenger Stanford | 2023/08/13 18:45 | Jason Jung v Keegan Smith | 5-7,6-4,6-1 |
| Challenger Stanford | 2023/08/12 20:20 | Quinn Vandecasteele v Keegan Smith | 5-7,7-6,3-6 |
| Challenger Cary | 2023/08/09 00:15 | Keegan Smith v Patrick Kypson | 3-6,2-6 |
| Challenger Cary | 2023/08/07 18:00 | Keegan Smith v Tyler Zink | 6-7,6-2,6-3 |
| Challenger Cary | 2023/08/06 19:10 | Nam Hoang Ly v Keegan Smith | 2-6,4-6 |
| ATP Los Cabos | 2023/07/31 04:20 | Beibit Zhukayev v Keegan Smith | 6-3,6-1 |
| ATP Los Cabos | 2023/07/30 01:00 | Keegan Smith v Patrick Kypson | 6-3,6-7,6-2 |
| ITF M15 Lakewood | 2023/07/14 20:10 | Learner Tien v Keegan Smith | 4-6,6-4,7-6 |
| ATP Winston-Salem | 2023/08/21 22:15 | Michael Mmoh v Darian King | 6-2,3-6,6-3 |
| ATP Winston-Salem | 2023/08/20 17:00 | Strong Kirchheimer v Darian King | 6-2,4-6,6-7 |
| ATP Winston-Salem | 2023/08/19 16:35 | Darian King v Ulises Blanch | 2-6,6-4,6-3 |
| Challenger Winnipeg | 2023/08/17 18:45 | Darian King v Ryan Peniston | 0-6,1-6 |
| Challenger Winnipeg | 2023/08/16 17:00 | Benjamin Bonzi v Darian King | 3-6,1-6 |
| Challenger Winnipeg | 2023/08/15 16:00 | Darian King v Brayden Schnur | 6-2,6-1 |
| Challenger Winnipeg | 2023/08/14 18:50 | Matija Pecotic v Darian King | 3-6,4-6 |
| Challenger Winnipeg | 2023/08/13 22:05 | Joshua Sheehy v Darian King | 6-3,1-6,3-6 |