Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| Challenger Chicago | 2023/07/11 15:00 | Altug Celikbilek v Tristan Schoolkate | 4-6,6-7 |
| Challenger Chicago | 2023/07/10 16:40 | Tristan Schoolkate v Christian Langmo | 6-3,1-6,7-5 |
| Challenger Chicago | 2023/07/09 21:30 | Tristan Schoolkate v Mukund Sasikumar | 6-4,6-1 |
| Challenger Bloomfield Hills | 2023/07/08 15:00 | Tristan Schoolkate v Steve Johnson | 4-6,2-6 |
| Challenger Bloomfield Hills | 2023/07/07 15:00 | Omar Jasika v Tristan Schoolkate | 4-6,3-6 |
| Challenger Bloomfield Hills | 2023/07/06 18:15 | Tristan Schoolkate v Altug Celikbilek | 7-6,7-5 |
| Challenger Bloomfield Hills | 2023/07/05 14:00 | Evan Zhu v Tristan Schoolkate | 7-6,2-6,4-6 |
| Challenger Bloomfield Hills | 2023/07/03 21:30 | Tristan Schoolkate v Andres Martin | 6-3,7-5 |
| Challenger Chicago | 2023/07/11 15:00 | Ernesto Escobedo v Ethan Quinn | 6-7,6-0,4-6 |
| Challenger Bloomfield Hills | 2023/07/05 14:00 | Mukund Sasikumar v Ethan Quinn | 7-5,4-6,7-6 |
| ITF M25 Tulsa | 2023/06/23 13:55 | Adam Walton v Ethan Quinn | 6-2,7-6 |
| ITF M25 Tulsa | 2023/06/21 14:00 | Karl Poling v Ethan Quinn | 6-7,6-3,6-7 |
| ITF M25 Wichita | 2023/06/18 17:00 | Ozan Baris v Ethan Quinn | 3-6,5-7 |
| ITF M25 Wichita | 2023/06/17 18:10 | Ethan Quinn v James Trotter | 7-6,7-5 |
| ITF M25 Wichita | 2023/06/16 14:45 | Ethan Quinn v Peter Bertran | 6-2,6-3 |
| ITF M25 Wichita | 2023/06/15 15:00 | Ethan Quinn v Aidan Kim | 6-4,6-1 |