Joao Cunha Silva defeated Emanuel Couto 6-1 7-5 in the Portugal 2 Masters 4 semi-final on clay. The upset overturned the form book — Emanuel Couto came in leading the head-to-head 2–0, but Joao Cunha Silva had been the form player, winning 7 of their last 10 on clay. Joao Cunha Silva claimed a first win over Emanuel Couto in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-01 | Portugal 1 Masters 2 | QF | clay | Emanuel Couto | 6-4 6-1 |
| 1997-02-01 | Portugal 2 Masters 3 | F | clay | Emanuel Couto | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.