Cipriano Pommies defeated Rafael Serpa Guinazu 7-6 6-2 in the Argentina 1 Masters 3 qualifying round 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 |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 1 | R32 | clay | Cipriano Pommies | 6-3 4-6 7-6 |