Nirupama Sanjeev defeated Jolene Watanabe 6-3 6-2 in the Peachtree 25K round of 32 on hard. The upset overturned the form book — Jolene Watanabe came in leading the head-to-head 1–0, but Nirupama Sanjeev had been the form player, winning 2 of their last 8 on hard. Nirupama Sanjeev claimed a first win over Jolene Watanabe in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Nashville 25K | R16 | hard | Jolene Watanabe | 6-2 6-2 |