Leonardo Olguin defeated Paulo Carvallo 7-6 6-0 in the Bolivia Paraguay Masters 3 semi-final on clay. Leonardo Olguin extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Paraguay F2 | QF | clay | Paulo Carvallo | 6-4 1-6 6-2 |
| 1999-04-10 | Chile 1 Masters 4 | SF | clay | Leonardo Olguin | 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.