Antonio Couvert defeated Alejandro Olivera 3-6 6-3 6-4 in the Uruguay F1 round of 32 on clay. Antonio Couvert extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-29 | Argentina 1 Masters 1 | R32 | clay | Antonio Couvert | 6-3 4-6 6-2 |
| 1998-05-02 | Chile 2 Masters 3 | R32 | clay | Alejandro Olivera | 4-6 6-1 7-6 |