Carlos Castellanos defeated Emilio Viuda Hernandez 6-3 6-2 in the Spain 1 2 round of 32 on clay. The upset overturned the form book — Emilio Viuda Hernandez came in leading the head-to-head 2–0, but Carlos Castellanos had been the form player, winning 3 of their last 8 on clay. Carlos Castellanos claimed a first win over Emilio Viuda Hernandez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-05 | Spain F1 | R32 | clay | Emilio Viuda Hernandez | 5-7 7-6 6-2 |
| 1999-01-29 | Spain 2 Masters 2 | R32 | clay | Emilio Viuda Hernandez | 6-4 1-6 7-5 |