Nuno Matias defeated Joao Cunha Silva 6-3 1-6 7-5 in the Portugal 1 4 round of 32 on clay. The upset overturned the form book — Joao Cunha Silva came in leading the head-to-head 4–0. Nuno Matias claimed a first win over Joao Cunha Silva in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-01 | Portugal 1 Masters 3 | R16 | clay | Joao Cunha Silva | 6-3 6-2 |
| 1999-05-01 | Portugal 1 Masters 4 | R32 | clay | Joao Cunha Silva | 6-3 7-5 |
| 1997-09-27 | Portugal 4 Masters 4 | R32 | carpet | Joao Cunha Silva | 6-2 6-3 |
| 1996-01-05 | Portugal 1 Masters 2 | R32 | clay | Joao Cunha Silva | 6-1 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.