Marco Osorio defeated Ivo Karlovic 6-4 7-6 in the Mexico F5 qualifying round on hard. The result followed the form book — Marco Osorio came in leading the head-to-head 1–0. Marco Osorio extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Mexico F7 | SF | hard | Marco Osorio | 6-2 3-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.