Kimberly Po Messerli defeated Lindsay Davenport 7-6 6-4 in the Australian Open round of 16 on hard. The upset overturned the form book — Lindsay Davenport came in leading the head-to-head 4–0. Kimberly Po Messerli claimed a first win over Lindsay Davenport in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-11-09 | Philadelphia | R16 | carpet | Lindsay Davenport | 6-1 6-2 |
| 1998-07-27 | Stanford | R16 | hard | Lindsay Davenport | 6-1 6-3 |
| 1998-05-25 | Roland Garros | R128 | clay | Lindsay Davenport | 6-2 6-2 |
| 1997-02-17 | Oklahoma | SF | hard | Lindsay Davenport | 1-6 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.