Patrick Sommer defeated Andrej Kracman 6-2 6-2 in the Portugal 3 Masters 2 semi-final on carpet. The upset overturned the form book — Andrej Kracman came in leading the head-to-head 1–0. Patrick Sommer claimed a first win over Andrej Kracman in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Lithuania F1 | SF | clay | Andrej Kracman | 6-2 6-3 |