Filippo Messori defeated Patricio Rudi 6-4 6-7 6-1 in the Chile F5 round of 32 on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 1–0. Filippo Messori extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Chile F4 | R32 | clay | Filippo Messori | 6-4 6-2 |