Roberto Menendez defeated David Caballero 1-4 4-2 5-4 4-5 4-2 in the Spain F9 qualifying round on clay. The result followed the form book — Roberto Menendez came in leading the head-to-head 1–0. Roberto Menendez extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-15 | Spain 7 Masters 3 | QF | clay | Roberto Menendez | 1-6 6-1 6-3 |