Carlos Castellanos defeated Roberto Menendez 2-6 6-2 6-4 in the Spain 4 4 qualifying round on clay. The upset overturned the form book — Roberto Menendez came in leading the head-to-head 2–0. Carlos Castellanos claimed a first win over Roberto Menendez in three meetings, narrowing 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) |
| 1997-05-09 | Spain 4 Masters 4 | R32 | clay | Roberto Menendez | 6-2 6-3 |