Roberto Menendez defeated Diego Hipperdinger 7-6 6-2 in the Spain 7 Masters 2 round of 32 on clay. The upset overturned the form book — Diego Hipperdinger came in leading the head-to-head 5–0. Roberto Menendez claimed a first win over Diego Hipperdinger in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-08-25 | Spain F20 | QF | clay | Diego Hipperdinger | 7-6(5) 6-3 |
| 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 |
| 1997-06-06 | Spain 5 Masters 4 | R32 | hard | Diego Hipperdinger | 6-7 6-2 6-2 |