Diego Hipperdinger defeated Roberto Menendez 7-6 6-3 in the Spain F20 qualifying round on clay. The result followed the form book — Diego Hipperdinger came in leading the head-to-head 4–1. Diego Hipperdinger extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-08-11 | Spain F18 | SF | clay | Diego Hipperdinger | 7-5 6-0 |
| 2002-09-23 | Spain F16 | R32 | hard | Diego Hipperdinger | 6-4 6-3 |
| 2001-02-05 | Spain 2 3 | R16 | clay | Diego Hipperdinger | 6-1 6-2 |
| 1999-10-15 | Spain 7 Masters 2 | R32 | clay | Roberto Menendez | 7-6 6-2 |
| 1997-06-06 | Spain 5 Masters 4 | R32 | hard | Diego Hipperdinger | 6-7 6-2 6-2 |