Ian Flanagan defeated David Sherwood 6-4 3-6 6-3 in the Great Britain 1 4 round of 16 on hard. The upset overturned the form book — David Sherwood came in leading the head-to-head 1–0. Ian Flanagan claimed a first win over David Sherwood in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-10-11 | Great Britain F7 | R32 | hard | David Sherwood | 6-2 6-2 |