Ivan Esquerdo defeated Santiago Ventura 6-1 7-5 in the Spain F5 round of 16 on clay. The upset overturned the form book — Santiago Ventura came in leading the head-to-head 2–1. Ivan Esquerdo narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-02-10 | Spain F2 | R16 | clay | Ivan Esquerdo | 6-4 7-6(5) |
| 2002-06-03 | Morocco F3 | QF | clay | Santiago Ventura | 6-4 4-6 6-4 |
| 2001-03-05 | Spain 3 2 | R16 | clay | Santiago Ventura | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.