Patricio Rudi defeated Miguel Tobon 7-5 6-3 in the Colombia F2 round of 16 on clay. The result followed the form book — Patricio Rudi came in leading the head-to-head 1–0. Patricio Rudi extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Paraguay F2 | R32 | clay | Patricio Rudi | 4-6 7-6 7-6 |