Luis Herrera defeated Leonardo Silva 6-4 6-4 in the Mexico F5 round of 16 on hard. The result followed the form book — Luis Herrera came in leading the head-to-head 1–0. Luis Herrera extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Mexico F4 | F | hard | Luis Herrera | 6-4 6-2 |