Alejandro Olivera defeated Hermes Gamonal 6-3 7-6 in the Chile 2 Masters 1 round of 16 on clay. The upset overturned the form book — Hermes Gamonal came in leading the head-to-head 1–0, but Alejandro Olivera had been the form player, winning 3 of their last 8 on clay. Alejandro Olivera claimed a first win over Hermes Gamonal in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Paraguay F3 | QF | clay | Hermes Gamonal | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.