Luis Hormazabal defeated Americo Venero Montes 7-5 6-3 in the Chile 1 Masters 2 round of 16 on clay. The upset overturned the form book — Americo Venero Montes came in leading the head-to-head 1–0, but Luis Hormazabal had been the form player, winning 3 of their last 7 on clay. Luis Hormazabal claimed a first win over Americo Venero Montes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 3 | R32 | clay | Americo Venero Montes | 7-5 2-6 6-4 |