Holly Parkinson advanced when Marissa Gould retired 6-2 4-1 in the Kirkland 75K qualifying round. Holly Parkinson claimed a first win over Marissa Gould in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-19 | Peachtree 25K | R32 | hard | Marissa Gould | 6-1 6-0 |
| 1999-06-14 | Mount Pleasant 25K | QF | hard | Marissa Gould | 6-2 6-4 |