Gustavo Cavallaro defeated Gaston Gaudio 6-4 6-3 in the Brazil 3 Masters 3 round of 16 on clay. The upset overturned the form book — Gaston Gaudio came in leading the head-to-head 3–0. Gustavo Cavallaro claimed a first win over Gaston Gaudio in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-11-02 | Uruguay Paraguay Masters 2 | R32 | clay | Gaston Gaudio | 7-6 7-5 |
| 1996-09-28 | Argentina 3 Masters 1 | R32 | clay | Gaston Gaudio | 6-3 7-6 |
| 1996-08-03 | Argentina 1 Masters 3 | QF | clay | Gaston Gaudio | 6-3 5-7 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.