Americo Venero Montes defeated Luis Hormazabal 7-5 2-6 6-4 in the Chile 1 Masters 3 round of 32 on clay. The upset overturned the form book — Luis Hormazabal came in leading the head-to-head 1–0. Americo Venero Montes claimed a first win over Luis Hormazabal in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 2 | R16 | clay | Luis Hormazabal | 7-5 6-3 |