Paulo Taicher defeated Jimy Szymanski 4-6 6-2 6-1 in the Cuba Mexico Masters 4 qualifying round on clay. The upset overturned the form book — Jimy Szymanski came in leading the head-to-head 1–0. Paulo Taicher claimed a first win over Jimy Szymanski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-20 | Cuba Mexico Masters 3 | SF | clay | Jimy Szymanski | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.