Zack Fleishman defeated Jeff Williams 6-3 0-6 6-3 in the USA F16 round of 32 on hard. Zack Fleishman extended 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 |
| 1999-09-10 | USA 2 Masters 3 | R16 | hard | Jeff Williams | 7-6 1-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.