Joao Cunha Silva defeated Nuno Marques 6-4 6-4 in the Portugal 1 Masters 2 round of 16 on clay. The upset overturned the form book — Nuno Marques came in leading the head-to-head 3–1. Joao Cunha Silva narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-01 | Portugal 1 Masters 3 | F | clay | Nuno Marques | 6-4 6-3 |
| 1998-01-31 | Portugal 1 Masters 1 | F | clay | Nuno Marques | 6-7 6-4 6-1 |
| 1995-01-06 | Portugal 1 Masters 3 | F | clay | Joao Cunha Silva | 7-5 4-6 6-3 |
| 1991-01-14 | Australian Open | R128 | hard | Nuno Marques | 4-6 6-4 1-6 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.