Sergi Duran defeated Jan Weinzierl 6-3 6-1 in the Spain 1 Masters 2 round of 16 on clay. The upset overturned the form book — Jan Weinzierl came in leading the head-to-head 1–0. Sergi Duran claimed a first win over Jan Weinzierl in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-02 | Spain 1 Masters 3 | R32 | clay | Jan Weinzierl | 7-6 2-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.