Desislava Topalova defeated Cindy Watson 2-6 7-5 7-6 in the Nuriootpa 25K round of 32 on hard. The result followed the form book — Desislava Topalova came in leading the head-to-head 1–0. Desislava Topalova extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Mount Gambier 25K | R32 | hard | Desislava Topalova | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.