Andre Lopes defeated Christian Persico 6-4 6-4 in the Portugal 2 Masters 4 round of 16 on carpet. The upset overturned the form book — Christian Persico came in leading the head-to-head 1–0. Andre Lopes claimed a first win over Christian Persico in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-02 | Portugal 2 Masters 3 | R32 | carpet | Christian Persico | 6-2 6-4 |