Karin Miller defeated Cindy Watson 6-2 6-4 in the Jackson 25K round of 32 on clay. The upset overturned the form book — Cindy Watson came in leading the head-to-head 2–0. Karin Miller claimed a first win over Cindy Watson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-31 | Surbiton 25K | R32 | grass | Cindy Watson | 7-6 3-6 6-4 |
| 1999-04-12 | Las Vegas 25K | R32 | hard | Cindy Watson | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.