Stadium: Court 1 Round: 26 Ground: Hardcourt indoor
| Challenger - Champaign | 2023/11/15 00:00 | Hunter Heck v Kenta Miyoshi | 3-6,4-6 |
| ITF - M15 Champaign | 2023/09/14 15:00 | Kenta Miyoshi v William Grant | 6-7,4-6 |
| ITF - M15 Champaign | 2023/09/13 15:00 | Taha Baadi v Kenta Miyoshi | 3-6,6-2,0-6 |
| ITF M25 - Southaven | 2023/08/08 18:30 | Kenta Miyoshi v Karlis Ozolins | 6-7,1-6 |
| ITF M25 Edwardsville | 2023/07/25 13:30 | Kenta Miyoshi v Gabrielius Guzauskas | 2-6,2-6 |
| ITF M25 Edwardsville | 2023/07/24 14:00 | Kenta Miyoshi v Oliver Okonkwo | 6-3,6-4 |
| ITF M25 Champaign | 2023/07/21 15:00 | Kenta Miyoshi v Naoki Nakagawa | 2-6,4-6 |
| ITF M25 Champaign | 2023/07/20 14:45 | Kenta Miyoshi v Cash Hanzlik | 6-3,3-6,6-2 |
| Challenger - Champaign | 2023/11/14 18:35 | Mark Whitehouse v Patrick Kypson | 1-6,6-7 |
| Challenger - Knoxville | 2023/11/07 15:00 | Denis Kudla v Patrick Kypson | 6-7,6-3,6-4 |
| Challenger - Charlottesville | 2023/11/04 17:30 | Beibit Zhukayev v Patrick Kypson | 6-4,7-6 |
| Challenger - Charlottesville | 2023/11/03 16:00 | Patrick Kypson v Brandon Holt | 6-1,6-4 |
| Challenger - Charlottesville | 2023/11/01 18:20 | Denis Kudla v Patrick Kypson | 1-6,3-6 |
| Challenger - Charlottesville | 2023/10/30 19:30 | Patrick Kypson v Gabriel Debru | 6-4,7-5 |
| Challenger - Fairfield | 2023/10/09 20:45 | Patrick Kypson v Aidan Mayo | 6-3,6-7,6-7 |
| Challenger - Tiburon | 2023/10/02 22:35 | Alexis Galarneau v Patrick Kypson | 7-6,6-4 |