Ground: Hardcourt outdoor
| UTR Pro Ann Arbor | 2023/07/29 20:00 | Ekansh Kumar v Jett Middleton | 6-3,6-3 |
| UTR Pro Ann Arbor | 2023/07/28 19:50 | Michael Ross v Jett Middleton | 6-1,6-1 |
| UTR Pro Ann Arbor | 2023/07/27 16:00 | Javier Rodriguez v Jett Middleton | 6-0,6-0 |
| UTR Pro Ann Arbor | 2023/07/25 15:00 | Tanapatt Nirundorn v Jett Middleton | 7-5,7-5 |
| UTR Pro Ann Arbor | 2023/07/24 22:06 | Jett Middleton v Jackson Ross | 3-6,3-5 |
| UTR Pro California | 2023/05/14 00:30 | Jett Middleton v Jeremy Field | 1-6,6-3,3-6 |
| UTR Pro California | 2023/05/11 20:00 | Jett Middleton v Tobias Luo | 7-5,6-2 |
| UTR Pro California | 2023/05/10 20:54 | Jett Middleton v Krish Arora | 6-4,6-7,6-7 |