Natasha Khan defeated Jade Windley 6-3 6-2 in the Portimao 10K round of 32 on hard. The upset overturned the form book — Jade Windley came in leading the head-to-head 2–0. Natasha Khan claimed a first win over Jade Windley in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-11-02 | Sunderland 10K | R32 | hard | Jade Windley | 6-0 6-4 |
| 2008-01-21 | Wrexham 10K | R32 | hard | Jade Windley | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.