Alejandro Olivera defeated Antonio Couvert 4-6 6-1 7-6 in the Chile 2 Masters 3 round of 32 on clay. The upset overturned the form book — Antonio Couvert came in leading the head-to-head 2–0. Alejandro Olivera claimed a first win over Antonio Couvert in three meetings, narrowing 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 |
| 1999-05-29 | Argentina 1 Masters 1 | R32 | clay | Antonio Couvert | 6-3 4-6 6-2 |