Patricio Rudi defeated Norbert Mazany 5-7 6-1 6-1 in the Uruguay F3 round of 32 on clay. The upset overturned the form book — Norbert Mazany came in leading the head-to-head 1–0. Patricio Rudi claimed a first win over Norbert Mazany in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-13 | Peru F3 | R32 | clay | Norbert Mazany | 6-1 7-5 |