Stadium: Court 13 Round: 25 Ground: Hardcourt outdoor
| Challenger Champaign | 2023/11/14 22:05 | Aleksandar Kovacevic v Cooper Williams | 6-3,2-6,6-4 |
| Challenger Champaign | 2023/11/13 16:00 | Evan Zhu v Cooper Williams | 7-5,4-6,5-7 |
| Challenger Champaign | 2023/11/12 16:00 | Cooper Williams v Pedro Vives Marcos | 6-2,6-2 |
| Challenger Charlottesville | 2023/10/29 15:25 | Evgeny Karlovskiy v Cooper Williams | 7-6,2-6,6-4 |
| Challenger Lexington | 2023/07/30 17:30 | Aidan Mayo v Cooper Williams | 6-4,6-3 |
| 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 | Makoto Ochi v Cooper Williams | 6-7,6-1,5-7 |
| Challenger Savannah | 2023/04/24 15:35 | Cooper Williams v Mateus Alves | 3-6,4-6 |
| Challenger Burnie | 2024/02/05 02:35 | Mikalai Haliak v Yusuke Takahashi | 1-6,7-6,3-6 |
| Challenger Burnie | 2024/01/30 23:00 | Yasutaka Uchiyama v Yusuke Takahashi | 6-2,6-4 |
| Challenger Burnie | 2024/01/29 03:55 | Jacob Bradshaw v Yusuke Takahashi | 6-7,6-7 |
| Challenger Nonthaburi | 2024/01/10 07:45 | Hiroki Moriya v Yusuke Takahashi | 7-6,6-1 |
| Challenger Nonthaburi | 2024/01/09 07:55 | Yusuke Takahashi v Henri Squire | 6-4,1-6,6-3 |
| Challenger Nonthaburi | 2024/01/08 05:50 | Yusuke Takahashi v Stefanos Sakellaridis | 7-6,6-3 |
| Challenger Nonthaburi | 2024/01/07 06:25 | Ergi Kirkin v Yusuke Takahashi | 3-6,4-6 |
| Challenger Yokkaichi | 2023/11/28 03:20 | Yusuke Takahashi v August Holmgren | 3-6,3-6 |