Jan Weinzierl defeated Ivan Rodrigo 6-1 6-4 in the Spain 6 4 round of 32 on clay. The upset overturned the form book — Ivan Rodrigo came in leading the head-to-head 2–0, but Jan Weinzierl had been the form player, winning 3 of their last 7 on clay. Jan Weinzierl claimed a first win over Ivan Rodrigo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-28 | Great Britain F5 | R32 | clay | Ivan Rodrigo | 6-1 6-2 |
| 1998-11-23 | Uruguay F1 | QF | clay | Ivan Rodrigo | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.