Louise Latimer defeated Karen Cross 5-7 6-1 6-1 in the Surbiton 25K round of 32 on grass. The upset overturned the form book — Karen Cross came in leading the head-to-head 1–0. Louise Latimer claimed a first win over Karen Cross in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Edinburgh 50K | R32 | clay | Karen Cross | 6-3 7-5 |