Stadium: Court 1 Round: 19 Ground: Hardcourt outdoor
| 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 Bloomfield Hills | 2023/07/02 18:00 | Tristan Schoolkate v Alafia Ayeni | 7-6,6-4 |
| Challenger Medellin | 2023/06/27 15:00 | Tristan Schoolkate v Eduardo Ribeiro | 2-6,6-7 |
| Challenger Chicago | 2023/07/09 17:20 | Nathan Ponwith v Christian Langmo | 4-6,5-7 |
| Challenger Bloomfield Hills | 2023/07/03 18:25 | Christian Langmo v Ozan Baris | 4-6,3-6 |
| Challenger Cali | 2023/06/20 23:30 | Alejandro Tabilo v Christian Langmo | 7-6,6-4 |
| Challenger Palmas del Mar | 2023/06/13 23:30 | Christian Langmo v Kei Nishikori | 2-6,4-6 |
| Challenger Tyler | 2023/06/08 16:00 | Christian Langmo v Adam Neff | 6-7,6-7 |
| Challenger Tyler | 2023/06/06 18:00 | Michael Mmoh v Christian Langmo | 3-6,6-7 |
| Challenger Tyler | 2023/06/05 18:45 | Dane Sweeny v Christian Langmo | 6-4,7-5 |
| Challenger Tyler | 2023/06/04 18:45 | Alafia Ayeni v Christian Langmo | 4-6,6-7 |