Chanda Rubin defeated Kristie Boogert 6-4 7-6 in the Canberra round of 32 on hard. Chanda Rubin extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R128 | grass | Kristie Boogert | 6-4 7-5 |
| 1999-01-04 | Auckland | R16 | hard | Chanda Rubin | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.