Juan Monaco defeated Ivan Esquerdo 4-6 6-2 6-1 in the Spain 5 1 round of 32 on clay. The upset overturned the form book — Ivan Esquerdo came in leading the head-to-head 1–0. Juan Monaco claimed a first win over Ivan Esquerdo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-06-17 | Spain F3 | R16 | hard | Ivan Esquerdo | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.