Israel Vior Diaz defeated Andrea Serra 6-1 6-7 6-1 in the Spain 6 Masters 4 round of 32 on clay. The upset overturned the form book — Andrea Serra came in leading the head-to-head 1–0. Israel Vior Diaz claimed a first win over Andrea Serra in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Spain F5 | R32 | clay | Andrea Serra | 0-6 7-5 6-3 |