Paulo Carvallo defeated Leonardo Olguin 6-4 1-6 6-2 in the Paraguay F2 qualifying round on clay. The upset overturned the form book — Leonardo Olguin came in leading the head-to-head 2–0. Paulo Carvallo claimed a first win over Leonardo Olguin in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-10 | Chile 1 Masters 4 | SF | clay | Leonardo Olguin | 7-5 |
| 1997-09-06 | Bolivia Paraguay Masters 3 | SF | clay | Leonardo Olguin | 7-6 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.