Joao Cunha Silva defeated Santiago Ventura 6-4 5-7 7-6 in the Portugal 2 Masters 2 semi-final on carpet. The result followed the form book — Joao Cunha Silva came in leading the head-to-head 1–0. Joao Cunha Silva extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-02 | Portugal 2 Masters 4 | F | carpet | Joao Cunha Silva | 6-3 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.