Ian Flanagan defeated Matthew Smith 6-4 7-6 in the Great Britain 1 4 qualifying round on hard. Ian Flanagan extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-09-25 | Great Britain F14 | R32 | hard | Matthew Smith | 7-5 2-6 6-4 |
| 2006-01-30 | Great Britain 1 2 | R32 | hard | Ian Flanagan | 7-5 6-1 |