Stadium: Court 7 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Edwardsville | 2023/07/28 00:00 | Cooper Williams v Quinn Vandecasteele | 3-6,4-6 |
| ITF M25 Edwardsville | 2023/07/26 14:00 | Quinn Vandecasteele v Blu Baker | 6-4,5-7,7-6 |
| ITF M25 Edwardsville | 2023/07/25 15:20 | Quinn Vandecasteele v Aurel Ciocanu | 6-1,6-4 |
| ITF M25 Edwardsville | 2023/07/24 17:00 | Quinn Vandecasteele v Jibril Nettles | 7-5,6-4 |
| Challenger Chicago | 2023/07/09 21:00 | Omar Jasika v Quinn Vandecasteele | 7-5,6-1 |
| ITF M15 Lakewood | 2023/07/07 19:00 | Alfredo Perez v Quinn Vandecasteele | 4-6,6-3,6-0 |
| ITF M15 Lakewood | 2023/07/06 18:30 | Quinn Vandecasteele v Omni Kumar | 0-6,7-5,7-5 |
| ITF M15 Lakewood | 2023/07/05 22:30 | Quinn Vandecasteele v Arthur Neuhaus | 6-3,6-3 |
| ITF M25 Edwardsville | 2023/07/28 00:00 | Micah Braswell v Naoki Nakagawa | 4-6,4-6 |
| ITF M25 Edwardsville | 2023/07/26 22:55 | Alexander Petrov v Naoki Nakagawa | 7-6,2-6,3-6 |
| ITF M25 Champaign | 2023/07/22 16:45 | Naoki Nakagawa v Aidan Mchugh | 4-6,4-6 |
| ITF M25 Champaign | 2023/07/21 15:00 | Kenta Miyoshi v Naoki Nakagawa | 2-6,4-6 |
| ITF M25 Champaign | 2023/07/19 14:55 | Karlis Ozolins v Naoki Nakagawa | 3-6,0-6 |
| ITF M25 Pensacola | 2023/05/18 18:55 | Naoki Nakagawa v Sekou Bangoura | 4-6,4-6 |
| ITF M25 Pensacola | 2023/05/17 16:15 | Naoki Nakagawa v Justin Lyons | 6-2,6-3 |
| Challenger Coquimbo | 2023/05/01 19:35 | Naoki Nakagawa v Pedro Boscardin Dias | 6-4,5-7,3-6 |