Zack Fleishman advanced when Michael Jessup retired 6-4 1-0 in the USA F15 qualifying round. Zack Fleishman extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-02-09 | San Jose | QF | hard | Zack Fleishman | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.