Henry Lieberman defeated Maxwell Benson 5-7 6-4 6-2 in the M15 Heraklion 10 round of 32 on hard. The result followed the form book — Henry Lieberman came in leading the head-to-head 1–0. Henry Lieberman extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-09-23 | M15 Heraklion 7 | Q16 | hard | Henry Lieberman | 6-7(2) 6-3 10-5 |