Ryan Sachire defeated Zack Fleishman 3-6 6-4 6-3 in the USA F9 round of 16 on hard. Ryan Sachire extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-06-10 | USA F14 | R16 | hard | Zack Fleishman | 6-3 6-2 |
| 1999-06-28 | USA F9 | R16 | hard | Ryan Sachire | 4-6 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.