Jolene Watanabe defeated Jean Okada 6-4 6-2 in the Austin TX 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 |
|---|---|---|---|---|---|
| 1999-10-18 | Nashville 25K | QF | hard | Jolene Watanabe | 6-4 4-6 7-5 |
| 1999-08-16 | Bronx 50K | R16 | hard | Jolene Watanabe | 6-3 6-3 |