Leonardo Olguin defeated Eduardo Medica 6-3 6-0 in the Argentina 4 qualifying round on clay. The upset overturned the form book — Eduardo Medica 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 |
|---|---|---|---|---|---|
| 2001-04-23 | Argentina F4 | QF | clay | Eduardo Medica | 6-3 6-2 |
| 2001-03-12 | Argentina F1 | R32 | clay | Leonardo Olguin | 6-3 6-4 |
| 1997-10-04 | Argentina 2 Masters 4 | R32 | clay | Eduardo Medica | 6-0 6-2 |
| 1996-08-31 | Argentina 2 Masters 1 | R16 | clay | Leonardo Olguin | 3-6 6-3 7-5 |
| 1996-08-03 | Argentina 1 Masters 2 | SF | clay | Eduardo Medica | 6-2 6-3 |
| 1995-04-01 | Argentina 1 Masters 3 | R32 | clay | Eduardo Medica | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.