Martin Stringari defeated Leonardo Olguin 6-3 6-4 in the Chile 1 Masters 3 round of 32 on clay. The upset overturned the form book — Leonardo Olguin came in leading the head-to-head 3–2. Martin Stringari narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-11-18 | Uruguay F2 | R32 | clay | Leonardo Olguin | 6-1 7-5 |
| 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 4 | R32 | clay | Leonardo Olguin | 4-6 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.