Henrique Wojciechowski Osorio defeated Goncalo Andrade 4-6 6-2 6-3 in the Portugal F9 qualifying round of 32 on clay. The upset overturned the form book — Goncalo Andrade came in leading the head-to-head 1–0. Henrique Wojciechowski Osorio claimed a first win over Goncalo Andrade in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-02-03 | Portugal F1 | Q64 | hard | Goncalo Andrade | 6-3 2-6 6-3 |