Stadium: Stadium Round: 14 Ground: Hardcourt outdoor
| 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 - South Bend M15 | 2023/06/25 15:00 | Strong Kirchheimer v James Tracy | 1-6,2-6 |
| ITF - South Bend M15 | 2023/06/24 14:55 | Strong Kirchheimer v Blaise Bicknell | 7-5,7-6 |
| ITF - South Bend M15 | 2023/06/23 18:10 | Strong Kirchheimer v Colton Smith | 3-6,7-6,6-3 |
| ITF - Decatur M25 | 2023/08/03 15:50 | Naoki Nakagawa v Quinn Vandecasteele | 6-4,6-1 |
| ITF - Decatur M25 | 2023/08/02 14:00 | Quinn Vandecasteele v Fabien Salle | 6-4,6-4 |
| ITF - Edwardsville M25 | 2023/07/30 14:30 | Aidan Mchugh v Quinn Vandecasteele | 3-6,6-7 |
| ITF - Edwardsville M25 | 2023/07/29 14:00 | Ozan Baris v Quinn Vandecasteele | 1-6,3-6 |
| ITF - Edwardsville M25 | 2023/07/28 14:30 | Quinn Vandecasteele v Naoki Nakagawa | 6-4,6-1 |
| ITF - Edwardsville M25 | 2023/07/28 00:00 | Cooper Williams v Quinn Vandecasteele | 3-6,4-6 |
| ITF - Edwardsville M25 | 2023/07/26 14:00 | Quinn Vandecasteele v Blu Baker | 6-4,5-7,7-6 |
| ITF - Edwardsville M25 | 2023/07/25 15:20 | Quinn Vandecasteele v Aurel Ciocanu | 6-1,6-4 |