Kepler Orellana defeated David Draper 7-6 6-2 in the Mexico 3 Masters 2 qualifying round on hard. The upset overturned the form book — David Draper came in leading the head-to-head 1–0. Kepler Orellana claimed a first win over David Draper in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-03-08 | Mexico 1 Masters 3 | R16 | hard | David Draper | 7-6 6-3 |