Matthew Smith defeated Alessandro Da Col 6-3 6-4 in the Great Britain F3 round of 16 on hard. The upset overturned the form book — Alessandro Da Col came in leading the head-to-head 1–0. Matthew Smith claimed a first win over Alessandro Da Col in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-10-11 | Great Britain F7 | R16 | hard | Alessandro Da Col | 6-3 5-7 6-4 |