Eduardo Frick defeated Diogo Cruz 4-6 7-6 6-0 in the Brazil F6 round of 32 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 | R32 | clay | Eduardo Frick | 6-4 3-6 6-4 |