Jeff Williams defeated Zack Fleishman 7-6 1-6 6-2 in the USA 2 Masters 3 round of 16 on hard. The upset overturned the form book — Zack Fleishman came in leading the head-to-head 2–0. Jeff Williams claimed a first win over Zack Fleishman in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-23 | Los Angeles | Q16 | hard | Zack Fleishman | 7-6(5) 6-4 |
| 2000-06-19 | USA F16 | R32 | hard | Zack Fleishman | 6-3 0-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.