Enzo Artoni defeated Patricio Rudi 3-6 6-4 6-2 in the Argentina 3 Masters 4 round of 32 on clay. The upset overturned the form book — Patricio Rudi came in leading the head-to-head 1–0. Enzo Artoni claimed a first win over Patricio Rudi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Paraguay F3 | QF | clay | Patricio Rudi | 6-3 7-5 |