Kimberly Po Messerli defeated Nathalie Tauziat 6-1 7-6 in the Canadian Open round of 64 on hard. The upset overturned the form book — Nathalie Tauziat came in leading the head-to-head 4–0. Kimberly Po Messerli claimed a first win over Nathalie Tauziat in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-05 | Filderstadt | R32 | hard | Nathalie Tauziat | 6-4 6-7 6-2 |
| 1998-08-17 | Canadian Open | R32 | hard | Nathalie Tauziat | 6-3 6-3 |
| 1997-10-12 | Zurich | R32 | hard | Nathalie Tauziat | 6-3 5-7 7-5 |
| 1997-08-04 | Manhattan Beach | R16 | hard | Nathalie Tauziat | 7-6 4-6 6-4 |