Gustavo Diaz defeated Leonardo Olguin 6-3 7-6 in the Argentina B Masters 2 round of 16 on clay. The upset overturned the form book — Leonardo Olguin came in leading the head-to-head 2–0. Gustavo Diaz claimed a first win over Leonardo Olguin in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-08-31 | Argentina 2 Masters 1 | R32 | clay | Leonardo Olguin | 6-4 7-6 |
| 1996-06-01 | Brazil 3 Masters 1 | R32 | clay | Leonardo Olguin | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.