Gabrio Castrichella defeated Alejandro Olivera 6-3 6-4 in the Uruguay Paraguay Masters 3 round of 32 on clay. The upset overturned the form book — Alejandro Olivera came in leading the head-to-head 1–0, but Gabrio Castrichella had been the form player, winning 5 of their last 8 on clay. Gabrio Castrichella claimed a first win over Alejandro Olivera in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-11-02 | Uruguay Paraguay Masters 4 | R16 | clay | Alejandro Olivera | 6-4 6-2 |