Matthew Smith defeated James May 7-5 7-6 in the Great Britain F9 round of 32 on hard. The result followed the form book — Matthew Smith came in leading the head-to-head 1–0. Matthew Smith extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-24 | Great Britain 4 1 | R16 | hard | Matthew Smith | 6-4 6-4 |