Daniel Caracciolo defeated Rodolfo Rake 6-7 6-4 6-2 in the Chile F8 semi-final on clay. The result followed the form book — Daniel Caracciolo came in leading the head-to-head 1–0. Daniel Caracciolo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Argentina F4 | R16 | clay | Daniel Caracciolo | 1-6 6-3 6-4 |