Zack Fleishman defeated Ryan Sachire 6-3 6-2 in the USA F14 round of 16 on hard. The upset overturned the form book — Ryan Sachire came in leading the head-to-head 2–0. Zack Fleishman claimed a first win over Ryan Sachire in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-15 | USA F9 | R16 | hard | Ryan Sachire | 3-6 6-4 6-3 |
| 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.