Leonardo Olguin defeated Leandro Rosa 7-6 7-5 in the Chile 1 Masters 4 round of 32 on clay. The result followed the form book — Leonardo Olguin came in leading the head-to-head 1–0. Leonardo Olguin extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Paraguay F2 | R32 | clay | Leonardo Olguin | 7-6 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.