Santiago Ventura defeated Raul Valdes 1-6 6-2 6-4 in the Spain 4 Masters 4 round of 32 on clay. The upset overturned the form book — Raul Valdes came in leading the head-to-head 1–0. Santiago Ventura claimed a first win over Raul Valdes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-04 | Spain 6 Masters 3 | R32 | clay | Raul Valdes | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.