Johan Settergren defeated Jan Hermansson 6-3 6-4 in the Great Britain F5 round of 32 on clay. The upset overturned the form book — Jan Hermansson came in leading the head-to-head 2–1. Johan Settergren narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-10 | Bastad | Q16 | clay | Jan Hermansson | 6-4 6-4 |
| 1999-02-10 | Great Britain F2 | R16 | carpet | Johan Settergren | 6-3 4-6 6-4 |
| 1998-09-28 | Sweden F2 | QF | hard | Jan Hermansson | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.