Jolene Watanabe defeated Rika Hiraki 6-3 4-6 7-5 in the Quebec City round of 32 on hard. The result followed the form book — Jolene Watanabe came in leading the head-to-head 1–0. Jolene Watanabe extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | Mahwah 50K | R32 | hard | Jolene Watanabe | 6-3 6-0 |