Ben Weintraub defeated Max Benaim 6-0 6-2 in the M25 Herzlia 1 round of 32 on hard. The upset overturned the form book — Max Benaim came in leading the head-to-head 1–0. Ben Weintraub claimed a first win over Max Benaim in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-06-19 | M25 Netanya 1 | Q32 | hard | Max Benaim | 7-5 6-3 |