Ian Flanagan defeated Matthew Illingworth 7-6 6-4 in the Great Britain F12 qualifying round on hard. The upset overturned the form book — Matthew Illingworth came in leading the head-to-head 1–0, but Ian Flanagan had been the form player, winning 2 of their last 5 on hard. Ian Flanagan claimed a first win over Matthew Illingworth in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-28 | Great Britain F11 | R32 | grass | Matthew Illingworth | 6-4 7-5 |