Dominique Monami defeated Martina Hingis 6-3 6-7 6-4 in the Filderstadt quarter-final on hard. The upset overturned the form book — Martina Hingis came in leading the head-to-head 5–0, defending the title, but Dominique Monami had been the form player, winning 6 of their last 10 on hard. Dominique Monami claimed a first win over Martina Hingis in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Filderstadt | QF | hard | Martina Hingis | 6-2 6-1 |
| 2000-07-31 | San Diego | R16 | hard | Martina Hingis | 6-2 7-6(2) |
| 2000-01-07 | Sydney | QF | hard | Martina Hingis | 6-1 RET |
| 1999-08-02 | San Diego | QF | hard | Martina Hingis | 6-2 6-4 |
| 1999-01-11 | Sydney | QF | hard | Martina Hingis | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.