Mathias Hellstrom defeated Jan Hermansson 4-6 6-2 6-1 in the Sweden Masters 3 qualifying round on carpet. The upset overturned the form book — Jan Hermansson came in leading the head-to-head 2–1. Mathias Hellstrom narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Greece F2 | QF | hard | Jan Hermansson | 6-3 6-2 |
| 1998-09-28 | Sweden F2 | F | hard | Mathias Hellstrom | 3-6 6-1 6-4 |
| 1998-09-14 | Norway F1 | SF | carpet | Jan Hermansson | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.