Natasha Khan defeated Anna Smith 6-7 6-2 6-4 in the Wrexham 10K qualifying round on hard. The upset overturned the form book — Anna Smith came in leading the head-to-head 2–0. Natasha Khan claimed a first win over Anna Smith in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-11 | London-Cumberland 10K | QF | hard | Anna Smith | 7-6(5) 6-1 |
| 2006-07-31 | Ilkley 10K | SF | grass | Anna Smith | 6-3 6-1 |