David Draper defeated Kepler Orellana 7-6 6-3 in the Mexico 1 Masters 3 round of 16 on hard. The upset overturned the form book — Kepler Orellana came in leading the head-to-head 1–0. David Draper claimed a first win over Kepler Orellana in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-24 | Mexico 3 Masters 2 | QF | hard | Kepler Orellana | 7-6 6-2 |