Roberto Menendez defeated David Caballero 1-6 6-1 6-3 in the Spain 7 Masters 3 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 |
|---|---|---|---|---|---|
| 2000-09-04 | Spain F9 | QF | clay | Roberto Menendez | 1-4 4-2 5-4(3) 4-5(3) 4-2 |