Leonardo Azzaro defeated Claudio Alvarado 6-3 6-2 in the Chile F5 round of 32 on clay. The upset overturned the form book — Claudio Alvarado came in leading the head-to-head 1–0, but Leonardo Azzaro had been the form player, winning 4 of their last 7 on clay. Leonardo Azzaro claimed a first win over Claudio Alvarado in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Chile F4 | R32 | clay | Claudio Alvarado | 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.