Jan Hermansson defeated Nicklas Timfjord 7-5 6-3 in the Sweden Masters 4 round of 16 on carpet. The upset overturned the form book — Nicklas Timfjord came in leading the head-to-head 2–0. Jan Hermansson claimed a first win over Nicklas Timfjord in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-17 | Great Britain F3 | R16 | carpet | Nicklas Timfjord | 6-3 6-4 |
| 1998-09-14 | Norway F1 | F | carpet | Nicklas Timfjord | 4-6 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.