Matthew Smith defeated Ian Flanagan 7-5 2-6 6-4 in the Great Britain F14 round of 32 on hard. The upset overturned the form book — Ian Flanagan came in leading the head-to-head 2–0, but Matthew Smith had been the form player, winning 4 of their last 8 on hard. Matthew Smith claimed a first win over Ian Flanagan in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-30 | Great Britain 1 2 | R32 | hard | Ian Flanagan | 7-5 6-1 |
| 2006-01-30 | Great Britain 1 4 | QF | hard | Ian Flanagan | 6-4 7-6(4) |