Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| Challenger Charleston | 2023/09/25 15:30 | Strong Kirchheimer v Elmer Moller | 6-1,6-3 |
| Challenger Charleston | 2023/09/24 15:30 | Strong Kirchheimer v Carter Pate | 6-0,6-1 |
| Challenger Columbus | 2023/09/19 17:45 | Strong Kirchheimer v Denis Kudla | 2-6,4-6 |
| Challenger Columbus | 2023/09/18 20:55 | Strong Kirchheimer v Alfredo Perez | 6-4,6-3 |
| Challenger Columbus | 2023/09/18 01:15 | Strong Kirchheimer v Kiranpal Pannu | 6-2,6-1 |
| Challenger Cary | 2023/09/13 23:20 | Strong Kirchheimer v Alex Michelsen | 3-6,1-6 |
| Challenger Cary | 2023/09/12 19:35 | Tristan Schoolkate v Strong Kirchheimer | 7-6,3-6,6-7 |
| Challenger Cary | 2023/09/11 17:00 | Strong Kirchheimer v Alex Rybakov | 6-7,7-5,7-6 |
| Challenger Charleston | 2023/09/26 13:30 | Stefan Dostanic v Alexander Ritschard | 6-4,6-4 |
| Challenger Charleston | 2023/09/25 17:05 | Stefan Dostanic v Stefan Kozlov | 6-2,6-1 |
| Challenger Charleston | 2023/09/25 14:00 | Evan Zhu v Stefan Dostanic | 6-4,5-7,0-6 |
| Challenger Cary | 2023/08/09 20:40 | Nicolas Moreno De Alboran v Stefan Dostanic | 6-2,7-6 |
| Challenger Cary | 2023/08/08 20:15 | Stefan Dostanic v Zachary Svajda | 7-6,6-3 |
| Challenger Cary | 2023/08/07 16:00 | Stefan Dostanic v Yuki Mochizuki | 3-6,6-3,6-1 |
| Challenger Cary | 2023/08/06 16:30 | Philip Sekulic v Stefan Dostanic | 5-7,6-4,1-6 |
| Challenger Lexington | 2023/08/01 14:00 | Bernard Tomic v Stefan Dostanic | 6-4,2-6,6-1 |