Roberto Alvarez defeated Daniel Caracciolo 6-3 6-2 in the Argentina F3 round of 32 on clay. The result followed the form book — Roberto Alvarez came in leading the head-to-head 1–0. Roberto Alvarez extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Argentina F4 | QF | clay | Roberto Alvarez | 6-4 0-6 7-5 |