Michelle Summerside defeated Courtenay Chapman 6-1 4-6 6-3 in the Jackson MS 25K round of 32 on clay. The result followed the form book — Michelle Summerside came in leading the head-to-head 1–0. Michelle Summerside extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-30 | Queretaro 10K | R32 | clay | Michelle Summerside | 6-2 6-3 |