Antonio Couvert defeated Emiliano Redondi 7-6 6-4 in the Argentina F3 round of 16 on clay. The upset overturned the form book — Emiliano Redondi came in leading the head-to-head 1–0. Antonio Couvert claimed a first win over Emiliano Redondi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Argentina F3 | R32 | clay | Emiliano Redondi | 7-5 4-6 7-5 |