Jimy Szymanski defeated Paulo Carvallo 6-2 6-7 6-3 6-4 in the PAR vs VEN round robin on clay. The result followed the form book — Jimy Szymanski came in leading the head-to-head 2–0. Jimy Szymanski extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-20 | Cuba Mexico Masters 1 | R16 | clay | Jimy Szymanski | 6-2 4-6 6-2 |
| 1999-02-20 | Cuba Mexico Masters 2 | R32 | clay | Jimy Szymanski | 7-6 6-2 |