Simon Roberts defeated Ian Flanagan 6-2 6-1 in the Great Britain 1 Satellite 3 round of 32 on hard. The upset overturned the form book — Ian Flanagan came in leading the head-to-head 1–0. Simon Roberts claimed a first win over Ian Flanagan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-09 | Great Britain F2 | R32 | hard | Ian Flanagan | 6-2 7-5 |