Alejandro Olivera defeated Gabrio Castrichella 6-4 6-2 in the Uruguay Paraguay Masters 4 round of 16 on clay. The upset overturned the form book — Gabrio Castrichella came in leading the head-to-head 1–0. Alejandro Olivera claimed a first win over Gabrio Castrichella in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-11-02 | Uruguay Paraguay Masters 3 | R32 | clay | Gabrio Castrichella | 6-3 6-4 |