Roberto Menendez defeated Carlos Castellanos 6-1 7-6 in the Spain F29 qualifying round on clay. Roberto Menendez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-07 | Spain 4 4 | QF | clay | Carlos Castellanos | 2-6 6-2 6-4 |
| 1997-05-09 | Spain 4 Masters 4 | R32 | clay | Roberto Menendez | 6-2 6-3 |