Kate Warne Holland defeated Louise Herbert 6-2 6-4 in the Frinton 10K round of 32 on grass. The upset overturned the form book — Louise Herbert came in leading the head-to-head 1–0. Kate Warne Holland claimed a first win over Louise Herbert in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Swansea 10K | R16 | clay | Louise Herbert | 6-0 6-4 |