Carlos Castellanos defeated Marc Canovas 7-5 6-3 in the Spain 3 4 round of 32 on clay. The result followed the form book — Carlos Castellanos came in leading the head-to-head 1–0. Carlos Castellanos extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-15 | Spain 7 Masters 1 | R32 | clay | Carlos Castellanos | 6-3 4-6 6-4 |