Maxime Boye defeated Andre Lopes 6-3 7-6 in the Portugal 3 Masters 3 round of 32 on carpet. The upset overturned the form book — Andre Lopes came in leading the head-to-head 1–0. Maxime Boye claimed a first win over Andre Lopes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-02 | Portugal 2 Masters 4 | R32 | carpet | Andre Lopes | 7-6 6-2 |