Kimberly Po Messerli defeated Barbara Schett 6-3 4-6 7-5 in the US Open round of 64 on hard. The upset overturned the form book — Barbara Schett came in leading the head-to-head 3–0. Kimberly Po Messerli claimed a first win over Barbara Schett in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R64 | clay | Barbara Schett | 6-3 3-6 6-1 |
| 1998-10-12 | Zurich | R32 | hard | Barbara Schett | 6-3 6-3 |
| 1997-03-20 | Key Biscayne | R32 | hard | Barbara Schett | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.