Leonardo Olguin defeated Gustavo Cavallaro 6-3 7-6 in the Argentina 1 Masters 4 round of 32 on clay. The upset overturned the form book — Gustavo Cavallaro came in leading the head-to-head 5–1, but Leonardo Olguin had been the form player, winning 5 of their last 8 on clay. Leonardo Olguin narrowed the head-to-head to 5–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-04-05 | Argentina 1 Masters 1 | R16 | clay | Leonardo Olguin | 6-4 4-6 7-6 |
| 1996-08-31 | Argentina 2 Masters 3 | R16 | clay | Gustavo Cavallaro | 6-4 6-3 |
| 1996-08-03 | Argentina 1 Masters 1 | R16 | clay | Gustavo Cavallaro | 6-2 2-6 6-1 |
| 1995-04-01 | Argentina 1 Masters 4 | R32 | clay | Gustavo Cavallaro | 7-6 6-2 |
| 1994-04-16 | Argentina 1 Masters 1 | R32 | clay | Gustavo Cavallaro | 6-4 7-5 |
| 1993-08-14 | Argentina 3 Masters 1 | R16 | clay | Gustavo Cavallaro | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.