Oscar Posada defeated Kepler Orellana 6-4 6-7 6-2 in the Venezuela F1 round of 16 on clay. The upset overturned the form book — Kepler Orellana came in leading the head-to-head 1–0. Oscar Posada claimed a first win over Kepler Orellana in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-13 | Jamaica F5 | R32 | hard | Kepler Orellana | 6-4 6-1 |