Rodrigo Pena defeated Leandro Rosa 1-6 7-5 6-4 in the Argentina 4 round of 32 on clay. The upset overturned the form book — Leandro Rosa came in leading the head-to-head 1–0. Rodrigo Pena claimed a first win over Leandro Rosa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 2 | R16 | clay | Leandro Rosa | 6-1 6-3 |