Gonzalo Fernandez defeated Daniel Caracciolo 6-4 7-6 in the Chile F1 round of 32 on clay. Gonzalo Fernandez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Chile F5 | QF | clay | Daniel Caracciolo | 6-4 6-4 |
| 1999-11-15 | Chile F4 | R32 | clay | Gonzalo Fernandez | 6-1 6-0 |