Ground: Hardcourt outdoor
| UTR Pro Knoxville | 2023/12/09 21:30 | Woodson Mcmillin v Vincent Rettke | 3-6,1-6 |
| UTR Pro Knoxville | 2023/12/08 19:00 | Younes Lalami Laaroussi v Woodson Mcmillin | 6-1,6-3 |
| UTR Pro Knoxville | 2023/12/08 00:22 | Przemyslaw Zielinski v Woodson Mcmillin | 4-6,0-6 |
| UTR Pro Knoxville | 2023/12/05 21:30 | Rohan Sachdev v Woodson Mcmillin | 3-6,6-4,6-0 |
| UTR Pro Knoxville | 2023/12/04 20:00 | Woodson Mcmillin v Christopher Li | 4-6,2-6 |
| UTR Pro Winston-Salem | 2023/12/01 18:55 | Maxwell Benson v Luca Pow | 3-6,5-7 |
| UTR Pro Winston-Salem | 2023/11/30 17:00 | Meecah Bigun v Maxwell Benson | 1-6,2-6 |
| UTR Pro Winston-Salem | 2023/11/29 17:00 | Jose Murariu v Maxwell Benson | 3-6,4-6 |
| UTR Pro Winston-Salem | 2023/11/28 18:00 | Alan Jesudason v Maxwell Benson | 4-6,5-7 |
| UTR Pro Winston-Salem | 2023/11/26 21:30 | Thomas Brown v Maxwell Benson | 6-2,6-0 |
| ITF M25 Saint-Augustin | 2023/10/24 13:55 | Maxwell Benson v Alex Finkelstein | 6-4,4-6,2-10 |
| ITF M25 Pazardzhik | 2023/10/02 13:15 | Plamen Milushev v Maxwell Benson | 6-4,7-5 |
| ITF M25 Pazardzhik | 2023/10/02 07:30 | Anthony Shumsky v Maxwell Benson | 2-6,3-6 |