Diego Hipperdinger defeated Ivan Esquerdo 4-6 6-2 6-4 in the Italy F7 qualifying round on clay. The result followed the form book — Diego Hipperdinger came in leading the head-to-head 2–0. Diego Hipperdinger extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-04-21 | Spain F8 | QF | clay | Diego Hipperdinger | 6-2 4-6 6-3 |
| 2000-07-10 | Spain F1 | R32 | clay | Diego Hipperdinger | 6-2 6-1 |