| 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 |
| ITF M25 Pazardzhik | 2023/09/27 12:35 | Nikola Kolyachev v Maxwell Benson | 6-4,7-6 |
| UTR Pro Winston-Salem | 2023/11/30 21:30 | Lukas Steffen v Luca Pow | 1-6,2-6 |
| UTR Pro Winston-Salem | 2023/11/29 21:30 | Saud Alhaqbani v Luca Pow | 3-6,1-6 |
| UTR Pro Winston-Salem | 2023/11/27 19:30 | Dhakshineswar Suresh v Luca Pow | 6-3,6-7,6-3 |
| UTR Pro Winston-Salem | 2023/11/26 17:00 | Luca Pow v Emmett Potter | 2-6,4-6 |
| ITF M15 Winston-Salem | 2023/11/07 16:00 | Luca Pow v Luca Staeheli | 5-7,4-6 |
| ITF M15 Winston-Salem | 2023/11/06 20:00 | Matthew Rankin v Luca Pow | 2-6,1-6 |
| UTR Pro Winston-Salem | 2023/09/08 21:43 | Franco Capalbo v Luca Pow | 6-2,6-4 |
| UTR Pro Winston-Salem | 2023/09/07 21:30 | Luca Pow v Joseph Wayand | 6-4,4-6,3-6 |