Ivan Esquerdo defeated Juan Monaco 6-1 6-4 in the Spain F3 round of 16 on hard. The upset overturned the form book — Juan Monaco came in leading the head-to-head 1–0. Ivan Esquerdo claimed a first win over Juan Monaco in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-05-07 | Spain 5 1 | R32 | clay | Juan Monaco | 4-6 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.