Leandro Rosa defeated Rodrigo Pena 6-1 6-3 in the Chile 1 Masters 2 round of 16 on clay. The upset overturned the form book — Rodrigo Pena came in leading the head-to-head 1–0. Leandro Rosa claimed a first win over Rodrigo Pena in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-12 | Argentina 4 | R32 | clay | Rodrigo Pena | 1-6 7-5 6-4 |