Jolene Watanabe defeated Louise Latimer 6-2 5-7 6-3 in the Mahwah 50K qualifying round on hard. The upset overturned the form book — Louise Latimer came in leading the head-to-head 1–0. Jolene Watanabe claimed a first win over Louise Latimer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-29 | Claremont 25K | R32 | hard | Louise Latimer | 6-4 6-4 |