Jacqueline Trail defeated Francesca Lubiani 2-6 6-3 6-4 in the Clearwater FL 25K round of 32 on hard. The upset overturned the form book — Francesca Lubiani came in leading the head-to-head 2–0, but Jacqueline Trail had been the form player, winning 5 of their last 9 on hard. Jacqueline Trail claimed a first win over Francesca Lubiani in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Albuquerque 50K | R32 | hard | Francesca Lubiani | 6-1 6-2 |
| 1999-02-15 | Midland 25K | QF | hard | Francesca Lubiani | 6-4 4-6 6-4 |