Jolene Watanabe defeated Holly Parkinson 6-2 5-7 7-5 in the Flushing 50K round of 32 on hard. The result followed the form book — Jolene Watanabe came in leading the head-to-head 2–0. Jolene Watanabe extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Lexington 50K | R16 | hard | Jolene Watanabe | 6-7 6-2 6-0 |
| 1999-02-15 | Midland 25K | R32 | hard | Jolene Watanabe | 6-3 6-3 |