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