Antonio Couvert defeated Alejandro Olivera 6-3 4-6 6-2 in the Argentina 1 Masters 1 round of 32 on clay. Antonio Couvert extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-19 | Uruguay F1 | R32 | clay | Antonio Couvert | 3-6 6-3 6-4 |
| 1998-05-02 | Chile 2 Masters 3 | R32 | clay | Alejandro Olivera | 4-6 6-1 7-6 |