Kirsty Woolley defeated Natasha Hillyer 6-3 6-2 in the Ilkley 10K round of 16 on grass. The upset overturned the form book — Natasha Hillyer came in leading the head-to-head 2–0. Kirsty Woolley claimed a first win over Natasha Hillyer in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-07 | Wrexham 10K | R32 | hard | Natasha Hillyer | 6-2 6-3 |
| 2005-08-29 | Nottingham 2 10K | R32 | hard | Natasha Hillyer | 6-2 6-2 |