Eduardo Frick defeated Ronaldo Carvalho 6-4 6-3 in the Brazil F4 round of 16 on clay. The result followed the form book — Eduardo Frick came in leading the head-to-head 1–0. Eduardo Frick extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Brazil F1 | R16 | clay | Eduardo Frick | 6-2 3-6 6-0 |