Raul Valdes defeated Santiago Ventura 6-3 6-4 in the Spain 6 Masters 3 round of 32 on clay. The upset overturned the form book — Santiago Ventura came in leading the head-to-head 1–0. Raul Valdes claimed a first win over Santiago Ventura in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-09 | Spain 4 Masters 4 | R32 | clay | Santiago Ventura | 1-6 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.