Jacqueline Trail defeated Joanne Moore 7-6 1-6 6-2 in the Hilton Head Island 10K semi-final on hard. The upset overturned the form book — Joanne Moore came in leading the head-to-head 1–0, but Jacqueline Trail had been the form player, winning 5 of their last 9 on hard. Jacqueline Trail claimed a first win over Joanne Moore in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Midlothian 25K | R32 | clay | Joanne Moore | 7-5 6-4 |