Patrick Sommer defeated Florian Jeschonek 5-7 6-3 6-4 in the Portugal 4 Masters 2 qualifying round on carpet. The result followed the form book — Patrick Sommer came in leading the head-to-head 1–0. Patrick Sommer extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Lithuania F1 | QF | clay | Patrick Sommer | 6-3 6-4 |