Patrick Sommer defeated Joao Cunha Silva 1-6 6-3 7-5 in the Portugal 3 Masters 2 round of 16 on carpet. The upset overturned the form book — Joao Cunha Silva came in leading the head-to-head 3–0. Patrick Sommer claimed a first win over Joao Cunha Silva in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-02 | Portugal 2 Masters 4 | QF | carpet | Joao Cunha Silva | 6-3 6-3 |
| 1997-09-27 | Portugal 4 Masters 3 | QF | carpet | Joao Cunha Silva | 6-3 6-7 6-2 |
| 1997-09-27 | Portugal 4 Masters 4 | SF | carpet | Joao Cunha Silva | 6-2 6-2 |