Leonardo Azzaro defeated Rodrigo Monte 6-2 6-4 in the Chile F6 round of 16 on clay. The upset overturned the form book — Rodrigo Monte came in leading the head-to-head 2–0, but Leonardo Azzaro had been the form player, winning 6 of their last 10 on clay. Leonardo Azzaro claimed a first win over Rodrigo Monte in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-29 | Portugal 1 4 | F | clay | Rodrigo Monte | 7-5 6-3 |
| 1999-06-19 | Italy 2 Masters 2 | R16 | clay | Rodrigo Monte | 7-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.