Mariano Campos defeated Sebastian Contador 6-3 7-6 in the Chile 2 Masters 3 round of 32 on clay. The upset overturned the form book — Sebastian Contador came in leading the head-to-head 1–0. Mariano Campos claimed a first win over Sebastian Contador in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Chile F2 | R32 | clay | Sebastian Contador | 7-5 6-4 |