Gilbert Schaller defeated Joao Cunha Silva 7-6 6-0 in the Umag round of 32 on clay. The upset overturned the form book — Joao Cunha Silva came in leading the head-to-head 1–0. Gilbert Schaller claimed a first win over Joao Cunha Silva in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-01 | Portugal 1 Masters 3 | SF | clay | Joao Cunha Silva | 6-7 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.