Jan Ralph Brandt defeated Patrik Fredriksson 6-1 3-6 6-4 in the Greece F3 qualifying round on hard. The upset overturned the form book — Patrik Fredriksson came in leading the head-to-head 1–0. Jan Ralph Brandt claimed a first win over Patrik Fredriksson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Israel F2 | R32 | hard | Patrik Fredriksson | 4-6 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.