Roberto Menendez defeated Carlos Castellanos 6-2 6-3 in the Spain 4 Masters 4 round of 32 on clay. Roberto Menendez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-12-01 | Spain F29 | QF | clay | Roberto Menendez | 6-1 7-6(2) |
| 2000-04-07 | Spain 4 4 | QF | clay | Carlos Castellanos | 2-6 6-2 6-4 |