Gabrio Castrichella defeated Kepler Orellana 6-3 3-6 6-3 in the Chile 2 Masters 1 round of 32 on clay. The result followed the form book — Gabrio Castrichella came in leading the head-to-head 1–0. Gabrio Castrichella extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Italy F6 | QF | clay | Gabrio Castrichella | 6-1 6-3 |