Guillermo Carry defeated Rafael Serpa Guinazu 6-2 6-0 in the Argentina F4 semi-final on clay. The upset overturned the form book — Rafael Serpa Guinazu came in leading the head-to-head 1–0. Guillermo Carry claimed a first win over Rafael Serpa Guinazu in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-29 | Argentina 1 Masters 1 | R32 | clay | Rafael Serpa Guinazu | 6-4 6-3 |