Josanne Van Bennekom advanced when Cindy Watson retired 3-6 0-1 in the Nuriootpa 25K round of 32. Josanne Van Bennekom claimed a first win over Cindy Watson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-26 | Rockhampton 25K | QF | hard | Cindy Watson | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.