Stadium: Court 6 Round: 54 Ground: Hardcourt indoor
| ITF M25 Pazardzhik | 2023/10/02 13:15 | Milushev, Plamen 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 |
| ITF M25 Pazardzhik | 2023/09/25 13:55 | Maxwell Benson v Felipe Mikkelsen | 7-6,6-4 |
| ITF M25 Pazardzhik | 2023/09/25 07:00 | Vojtech Vlkovsky v Maxwell Benson | 3-6,0-6 |
| ITF M25 Pardubice | 2023/09/18 10:30 | Tom Schonenberg v Maxwell Benson | 6-1,6-2 |
| ITF M25 Pardubice | 2023/09/17 12:00 | Vagner, Josef v Maxwell Benson | 4-6,2-6 |
| ITF M15 Satu Mare | 2023/09/12 07:00 | Juan Cruz Martin Manzano v Maxwell Benson | 7-6,6-3 |
| ITF M25 Saint-Augustin | 2023/10/23 16:00 | Andres Valentin Ispas v Alex Finkelstein | 6-2,2-6,3-10 |
| ITF M15 Ithaca | 2023/10/02 14:00 | Alex Finkelstein v Aurel Ciocanu | 1-6,6-7 |
| UTR Pro Denver | 2023/09/02 17:25 | Alex Finkelstein v Sam De Vries | 7-6,3-6,2-6 |
| UTR Pro Denver | 2023/09/01 19:00 | Alex Finkelstein v Fox, David | 6-3,5-1 |
| UTR Pro Denver | 2023/08/31 21:35 | Alex Finkelstein v Nicolas H Cuesta | 5-7,2-6 |
| UTR Pro Denver | 2023/08/30 23:30 | Daniel Sancho Arbizu v Alex Finkelstein | 6-0,6-6 |
| UTR Pro Denver | 2023/08/29 21:07 | Sanjeev Chundu v Alex Finkelstein | 6-1,6-2 |
| ITF M25 Southaven | 2023/08/08 13:55 | Chopra, Keshav v Alex Finkelstein | 6-1,6-2 |