Ian Flanagan defeated Simon Roberts 6-2 7-5 in the Great Britain F2 round of 32 on hard. The upset overturned the form book — Simon Roberts came in leading the head-to-head 1–0, but Ian Flanagan had been the form player, winning 3 of their last 8 on hard. Ian Flanagan claimed a first win over Simon Roberts in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-01-31 | Great Britain 1 Satellite 3 | R32 | hard | Simon Roberts | 6-2 6-1 |