Matthew Illingworth defeated Ian Flanagan 6-4 7-5 in the Great Britain F11 round of 32 on grass. The upset overturned the form book — Ian Flanagan came in leading the head-to-head 1–0. Matthew Illingworth claimed a first win over Ian Flanagan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-04 | Great Britain F12 | QF | hard | Ian Flanagan | 7-6(7) 6-4 |