Matthew Smith defeated James May 6-4 6-4 in the Great Britain 4 1 round of 16 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 |
|---|---|---|---|---|---|
| 2003-09-15 | Great Britain F9 | R32 | hard | Matthew Smith | 7-5 7-6(3) |