Federico Dondo defeated Daniel Caracciolo 7-5 6-4 in the Uruguay Masters 2 round of 16 on clay. The result followed the form book — Federico Dondo came in leading the head-to-head 1–0. Federico Dondo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Netherlands Masters 3 | QF | clay | Federico Dondo | 6-3 6-2 |