Stadium: Center Court Round: 14 Ground: Hardcourt outdoor
| 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 South Bend | 2023/06/23 18:10 | Strong Kirchheimer v Colton Smith | 3-6,7-6,6-3 |
| ITF M15 South Bend | 2023/06/22 17:35 | Strong Kirchheimer v Karlis Ozolins | 6-7,7-6,6-4 |
| ITF M15 South Bend | 2023/06/21 16:30 | Strong Kirchheimer v Jacob Bickersteth | 6-2,6-2 |
| Challenger Palmas del Mar | 2023/06/12 16:35 | Bernard Tomic v Strong Kirchheimer | 7-5,3-6,6-3 |
| Challenger Palmas del Mar | 2023/06/11 20:05 | Gage Brymer v Strong Kirchheimer | 4-6,4-6 |
| Challenger Bloomfield Hills | 2023/07/03 20:50 | Evan Zhu v Colin Sinclair | 7-5,1-6,6-2 |
| Challenger Bloomfield Hills | 2023/07/03 14:15 | Patrick Maloney v Colin Sinclair | 7-6,6-7,3-6 |
| ITF M25 Tulsa | 2023/06/20 16:00 | Adam Neff v Colin Sinclair | 4-6,7-5,7-5 |
| Challenger Palmas del Mar | 2023/06/14 15:00 | Liam Draxl v Colin Sinclair | 7-6,6-3 |
| Challenger Palmas del Mar | 2023/06/13 20:00 | Colin Sinclair v Alexander Bravo | 6-2,6-0 |
| Challenger Palmas del Mar | 2023/06/12 15:00 | Kaito Uesugi v Colin Sinclair | 1-6,6-7 |
| Challenger Palmas del Mar | 2023/06/11 18:40 | Henrik Wiersholm v Colin Sinclair | 2-6,1-6 |
| ITF M15 Rancho Santa Fe | 2023/06/04 20:05 | Colin Sinclair v Jaimee Floyd Angele | 6-3,6-2 |