Jane Chi defeated Allison Bradshaw 6-2 6-3 in the Tucson Challenger round of 16 on hard. The upset overturned the form book — Allison Bradshaw came in leading the head-to-head 1–0. Jane Chi claimed a first win over Allison Bradshaw in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-05 | Hilton Head Island 10K | QF | hard | Allison Bradshaw | 7-5 6-1 |