Kepler Orellana defeated Ryan Sachire 6-3 6-4 in the USA F9 qualifying round on hard. The upset overturned the form book — Ryan Sachire came in leading the head-to-head 1–0. Kepler Orellana claimed a first win over Ryan Sachire in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-03-22 | USA F8 | R16 | hard | Ryan Sachire | 7-5 6-3 |