Leonardo Olguin defeated Martin Stringari 6-1 7-5 in the Uruguay F2 round of 32 on clay. The upset overturned the form book — Martin Stringari came in leading the head-to-head 4–2, but Leonardo Olguin had been the form player, winning 5 of their last 8 on clay. Leonardo Olguin narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-11-16 | Brazil 5 Masters 2 | QF | clay | Leonardo Olguin | 6-4 5-7 7-6 |
| 1996-09-28 | Argentina 3 Masters 4 | QF | clay | Martin Stringari | 6-4 4-6 6-0 |
| 1996-06-01 | Brazil 3 Masters 1 | R16 | clay | Martin Stringari | 6-2 3-6 6-2 |
| 1996-06-01 | Brazil 3 Masters 2 | R16 | clay | Martin Stringari | 6-4 6-3 |
| 1996-06-01 | Brazil 3 Masters 4 | R32 | clay | Leonardo Olguin | 4-6 6-4 6-2 |
| 1996-03-23 | Chile 1 Masters 3 | R32 | clay | Martin Stringari | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.