Hermes Gamonal defeated Enzo Artoni 6-4 6-3 in the Chile 1 Masters 4 round of 16 on clay. The upset overturned the form book — Enzo Artoni came in leading the head-to-head 1–0, but Hermes Gamonal had been the form player, winning 4 of their last 10 on clay. Hermes Gamonal claimed a first win over Enzo Artoni in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Chile F4 | R16 | clay | Enzo Artoni | 6-3 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.