Stadium: Court 19 Round: 25 Ground: Clay
| Challenger Yokkaichi | 2023/11/27 01:00 | Nathan Ponwith v James Trotter | 1-6,2-6 |
| Challenger Yokkaichi | 2023/11/26 01:00 | Nathan Ponwith v Kazuma Kawachi | 6-7,6-4,7-5 |
| Challenger Yokohama | 2023/11/19 07:55 | Nathan Ponwith v Colin Sinclair | 3-6,6-7 |
| Challenger Champaign | 2023/11/12 19:35 | Nathan Ponwith v Murphy Cassone | 5-7,3-6 |
| Challenger Knoxville | 2023/11/05 19:25 | Alex Rybakov v Nathan Ponwith | 6-4,6-4 |
| ITF M25 Harlingen | 2023/10/25 13:55 | Nathan Ponwith v Marcus McDaniel | 5-7,4-6 |
| ITF M15 Las Vegas | 2023/10/18 16:55 | Nathan Ponwith v Sebastian Dominko | 3-6,6-7 |
| Challenger Fairfield | 2023/10/08 20:05 | Edward Winter v Nathan Ponwith | 6-2,6-2 |
| 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 |