Rodrigo Pena defeated Daniel Wajnberg 7-6 6-2 in the Chile 2 Masters 3 round of 32 on clay. The upset overturned the form book — Daniel Wajnberg came in leading the head-to-head 1–0, but Rodrigo Pena had been the form player, winning 1 of their last 5 on clay. Rodrigo Pena claimed a first win over Daniel Wajnberg in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-08-10 | Ecuador F2 | R32 | clay | Daniel Wajnberg | 6-4 7-5 |