Oscar Bustos defeated Cipriano Pommies 6-2 6-7 6-2 in the Chile F3 round of 16 on clay. The upset overturned the form book — Cipriano Pommies came in leading the head-to-head 1–0. Oscar Bustos claimed a first win over Cipriano Pommies in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 4 | QF | clay | Cipriano Pommies | 6-3 6-4 |