Zack Fleishman defeated Doug Root 6-3 6-1 in the USA F23 round of 32 on hard. The result followed the form book — Zack Fleishman came in leading the head-to-head 1–0. Zack Fleishman extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | USA F13 | QF | hard | Zack Fleishman | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.