Jan Weinzierl defeated Sergi Duran 7-6 2-6 6-3 in the Spain 1 Masters 3 round of 32 on clay. The upset overturned the form book — Sergi Duran came in leading the head-to-head 1–0. Jan Weinzierl claimed a first win over Sergi Duran in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-02 | Spain 1 Masters 2 | R16 | clay | Sergi Duran | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.