Ruben Gajardo defeated Enzo Artoni 6-3 6-4 in the Chile 1 Masters 1 round of 32 on clay. The upset overturned the form book — Enzo Artoni came in leading the head-to-head 1–0, but Ruben Gajardo had been the form player, winning 4 of their last 10 on clay. Ruben Gajardo claimed a first win over Enzo Artoni in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-03 | Chile 1 Masters 3 | R16 | clay | Enzo Artoni | 6-3 7-5 |