Cipriano Pommies defeated Rafael Serpa Guinazu 6-3 4-6 7-6 in the Chile 1 Masters 1 round of 32 on clay. The result followed the form book — Cipriano Pommies came in leading the head-to-head 1–0. Cipriano Pommies extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-29 | Argentina 1 Masters 3 | QF | clay | Cipriano Pommies | 7-6 6-2 |