Claire Taylor defeated Helen Crook 6-0 3-6 6-3 in the Frinton 10K round of 16 on grass. The upset overturned the form book — Helen Crook came in leading the head-to-head 1–0. Claire Taylor claimed a first win over Helen Crook in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Sunderland 10K | R32 | hard | Helen Crook | 1-6 7-5 6-1 |