Daniel Caracciolo defeated Diego Palmeiro 6-3 6-2 in the Portugal 3 Masters 2 round of 32 on hard. 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 |
|---|---|---|---|---|---|
| 1997-11-01 | Uruguay Masters 3 | R16 | clay | Daniel Caracciolo | 6-2 6-4 |