Ryan Sachire defeated Kepler Orellana 7-5 6-3 in the USA F8 round of 16 on hard. The upset overturned the form book — Kepler Orellana came in leading the head-to-head 1–0, but Ryan Sachire had been the form player, winning 4 of their last 6 on hard. Ryan Sachire claimed a first win over Kepler Orellana in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-03-29 | USA F9 | QF | hard | Kepler Orellana | 6-3 6-4 |