Ground: Clay
| UTR Pro Yokohama | 2025/03/07 05:05 | Christopher Kosei Ono v Maxwell Benson | 2-6,3-6 |
| UTR Pro Yokohama | 2025/03/07 00:00 | Haruki Katsushima v Maxwell Benson | 5-7,2-6 |
| UTR Pro Yokohama | 2025/03/06 04:55 | Maxwell Benson v Steffan Van Weldam | 6-4,6-4 |
| UTR Pro Yokohama | 2025/03/06 01:45 | Maxwell Benson v Kotaro Mochizuki | 4-6,3-6 |
| UTR Pro Yokohama | 2025/03/04 00:30 | Maxwell Benson v Haruto Ishikawa | 6-3,6-3 |
| ITF M15 Tallahassee | 2024/11/19 14:00 | Daniel Milavsky v Maxwell Benson | 6-0,6-4 |
| ITF M15 Boca Raton | 2024/11/11 16:30 | Maxwell Benson v Cyrus Mahjoob | 0-6,0-6 |
| ITF M25 Norman | 2024/10/21 18:00 | Bruno Nhavene v Maxwell Benson | 6-7,7-6,10-3 |
| UTR Pro Boca Raton | 2025/03/31 13:00 | Kalman Boyd v Dakotah Bobo | 3-6,6-3,4-6 |
| UTR Pro Boca Raton | 2025/03/29 17:40 | Dakotah Bobo v William Hsieh | 6-4,7-5 |
| UTR Pro Boca Raton | 2025/03/28 16:25 | Jaden Brady v Dakotah Bobo | 4-6,2-6 |
| UTR Pro Boca Raton | 2025/03/27 17:20 | Ethan Schiffman v Dakotah Bobo | 6-4,6-2 |
| UTR Pro Boca Raton | 2025/03/25 16:55 | Lucca Acioly v Dakotah Bobo | 1-6,2-6 |
| UTR Pro Boca Raton | 2025/03/24 22:10 | Dakotah Bobo v Mwendwa Mbithi | 3-6,2-6 |
| ITF M15 Boca Raton | 2024/11/12 15:30 | Dakotah Bobo v Maximus Dussault | 4-6,6-4,5-10 |
| ITF M15 Boca Raton | 2024/11/11 15:00 | Adriano Dzhenev v Dakotah Bobo | 7-5,4-6,4-10 |